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Korean Chemical Society (대한화학회)
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A Development of Rapid, Practical and Selective Process for Preparation of Z-Oximes

  • Kim, Bo Ram (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Sciences, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Sung, Gi Hyeon (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Sciences, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Kim, Jeum-Jong (Advanced Solar Technology Research Department, Electronic and Telecommunications Research Institute) ;
  • Yoon, Yong-Jin (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Sciences, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
  • Received : 2012.12.28
  • Accepted : 2013.01.22
  • Published : 2013.04.20
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Abstract

Keywords

EXPERIMENTAL

Melting points were determined with a capillary apparatus and uncorrected. NMR spectra were recorded on a 300MHz spectrometer with chemical shift values reported in units (ppm) relative to an internal standard (TMS). IR spectra were obtained on SIMADZU FT-IR 8400s spectrophotometer. The open-bed chromatography was carried out on silica gel (70−230 mesh, Merck) using gravity flow. The column was packed with slurries made from the elution solvent.

General Procedure for the Conversion of Aldehydes and Ketones to Oximes

A mixture of carbonyl compound (1a−1l, 8.3 mmol), hydroxylamine hydrochloride (8.4 mmol), K2CO3 (9.1 mmol) and MeOH (40 ml) was stirred at until the carbonyl compound was disappeared at reflux temperature or at room temperature. After cooling to room temperature, ketoximes 2a−2f were extracted with dichloromethane (30 × 5 mL). The organic layer was separated and dried over anhydrous MgSO4. After evaporating the solvent under reduced pressure at below 20 ℃, the isomers were then separated from the resulting residue by column chromatography [n-hexane : ethyl acetate = 3 : 1 (v/v)] to give the corresponding E- and Z-ketoximes. (Caution: E- ketoxime is evaporating the solvent below 20 ℃. And store in freezer).

In the case of aldoximes, the solvent was evaporated under reduced pressure. The resulting residue was washed with cold diethyl ether (150 mL). The ether solutions were combined, and evaporated under reduced pressure. The isomers were then separated by column chromatography [n-hexane : ethyl acetate = 3 : 1 (v/v)] to give the corresponding E- and Z-aldoximes.

(E)-Acetophenone oxime (E-2a)

Mp 75−76 ℃ (lit.18 80−81 ℃); Rf = 0.23 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3193, 3083, 3053, 3030, 2967, 2920, 2868, 1468, 1436, 1375, 1301, 1267, 1021, 950, 759, 693, 621 cm−1; 1H NMR (300 MHz, CDCl3): δ 3.31 (s, 3H), 7.36−7.42 (m, 3H), 7.60−7.64 (m, 2H); 13C NMR (75 MHz, CDCl3): δ 12.37, 126.0, 128.5, 129.3, 136.4, 156.1; HRMS(EI): m/z calcd for C8H9NO: 135.0684; found: 135.0684.

(Z)-Acetophenone oxime (Z-2a)

Mp 52−54 ℃ (lit.19 52−55 ℃); Rf = 0.3 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3292, 3245, 3064, 2926, 1496, 1446, 1370, 1302, 1265, 1079, 1006, 926, 762, 744 cm−1; 1H NMR (300 MHz, CDCl3): δ 2.30 (s, 3H), 7.36 (m, 3H), 7.60−7.62 (m, 2H), 9.86 (s, OH, D2O exchangeable ); 13C NMR (75 MHz, CDCl3): δ 12.42, 126.0, 128.5, 129.2, 136.4, 155.9; HRMS (EI): m/z calcd for C8H9NO: 135.0684; found: 135.0684.

(E)-4-Bromoacetophenone oxime (E-2b)

Mp 115−116 ℃; Rf = 0.2 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3199, 3087, 3054, 2090, 2869, 2838, 1585, 1488, 1460, 1423, 1392, 1264, 1089, 1029, 1010, 942, 820, 748 cm−1; 1H NMR (300 MHz, CDCl3) : δ 2.27 (s, 3H), 7.25−7.56 (m, 4H); 13C NMR (75 MHz, CDCl3): δ 12.22, 123.6, 127.6, 131.6, 135.2, 155.2(9); HRMS (EI): m/z calcd for C8H8NOBr: 212.9789; found: 212.9793.

(Z)-4-Bromoacetophenone oxime (Z-2b)

Mp 124−126 ℃; Rf = 0.48 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3286, 3246, 3082, 3009, 3956, 2914, 1484, 1394, 1309, 1274, 1182, 1069, 1008, 929, 825, 750 cm−1; 1H NMR (300 MHz, CDCl3): δ 2.27 (s, 3H), 7.24−7.52 (m, 4H), 8.72 (s, OH D2O exchangeable); 13C NMR (75 MHz, CDCl3): δ 12.25, 123.6, 127.6, 131.7, 135.2, 155.2(5); HRMS (EI): m/z calcd for C8H8NOBr: 212.9789; found: 212.9793.

(E)-3,4-Dimethoxyacetophenone oxime (E-2c)

Mp 45−47 ℃; Rf = 0.11 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3249, 3005, 2954, 2921, 2851, 1517, 1463, 1416, 1367, 1274, 1260, 1225, 1175, 1148, 1024, 948, 869, 804, 764, 749 cm−1; 1H NMR (300 MHz, DMSO-d6) : δ 2.10 (s, 3H), 3.75 (d, 6H, J = 9.9 Hz), 6.95−7.31 (m, 3H), 10.59 (s, OH, D2O exchangeable); 13C NMR (75 MHz, DMSO-d6) : δ 21.87, 55.39, 55.45, 110.9, 111.6, 112.3, 121.3, 147.7, 150.1, 158.1; HRMS(EI): m/z calcd for C10H13NO3: 195.0895; found: 195.0899.

(Z)-3,4-Dimethoxyacetophenone oxime (Z-2c)

Mp 141−143 ℃; Rf = 0.17 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3432, 3084, 3011, 2975, 2928, 2843, 1583, 1515, 1503, 1456, 1441, 1332, 1296, 1272, 1241, 1222, 1173, 1149, 1079, 1016, 998, 950, 869, 812, 766 cm−1; 1H NMR (300 MHz, DMSO-d6) : δ 2.14 (s, 3H), 3.77 (s, 6H), 6.93−6.95 (m, 1H), 7.14−7.17 (m, 1H), 7.28(2)−7.28(4) (m, 1H), 11.03 (s, OH D2O exchangeable); 13C NMR (75 MHz, DMSO-d6): δ 11.33, 55.22, 55.38, 108.2, 111.1, 118.4, 129.5, 148.4, 149.4, 152.3; HRMS(EI): m/z calcd for C10H13NO3: 195.0895; found: 195.0899.

(E)-4-Methylpentan-2-one oxime (E-2d)

Liquid; Rf = 0.35 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 1341, 1265, 1215, 1165, 1108, 1017, 955, 803, 751 cm−1; 1H NMR (300 MHz, CDCl3): δ 0.94 (d, 6H, J = 6.6 Hz), 1.86(0)−1.86(9) (m, 4H), 2.25 (d, 2H, J = 7.5 Hz), 8.56 (s, OH, D2O exchangeable); 13C NMR (75 MHz, CDCl3): δ 14.10, 25.73, 26.90, 37.44, 158.3; HRMS(EI): m/z calcd for C6H13NO: 115.0997; found: 115.1008.

(Z)-4-Methylpentan-2-one oxime (Z-2d)

Liquid; Rf = 0.55 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3422, 2958, 2375, 1629, 1464, 1374, 1112, 974, 931, 875, 832, 736 cm−1; 1H NMR (300 MHz, CDCl3): δ 0.91 (d, 6H, J = 6.6 Hz ), 1.82−1.94 (m, 4H), 2.06 (d, 2H, J = 7.2 Hz), 9.74 (s, OH, D2O exchangeable); 13C NMR (75 MHz, CDCl3): δ 13.56, 22.36, 25.85, 44.75, 157.9; HRMS(EI): m/z calcd for C6H13NO: 115.0997; found: 115.1008.

Cyclohexanone oxime (2e)

Mp 85−87 ℃ (lit.20 85−87 ℃); Rf = 0.5 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3232, 3114, 2933, 2856, 2729, 1600, 1477, 148, 1249, 1222, 991, 958, 896, 763, 655, 565, 474 cm−1; 1H NMR (300 MHz, CDCl3): δ 1.56−1.71 (m, 6H), 2.20−2.25 (m, 2H), 2.49−2.53 (m, 2H), 8.54 (s, 1H); 13C NMR (75 MHz, CDCl3): δ 24.51, 25.57, 25.77, 26.86, 32.08, 160.89; HRMS (EI): m/z calcd for C6H11NO: 113.0841; found: 113.0848.

Benzophenone oxime (2f)

Mp 136−137 ℃ (lit.21 138−142 ℃); Rf = 0.45 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3253, 3055, 2953, 2923, 2854, 1448, 1327, 1077, 1032, 997, 919, 766, 697 cm−1; 1H NMR (300 MHz, DMSO-d6): δ 7.26−7.29 (m, 2H), 7.37−7.38 (m, 5H), 7.41−7.49 (m, 3H), 11.34 (s, 1H); 13C NMR (75 MHz, DMSO-d6): δ 127.4, 128.6, 128.8(0), 128.8(4), 129.3, 133.9, 137.1, 147.3, 155.6; HRMS(EI): m/z calcd for C13H11NO: 197.0841; found: 197.0844.

(E)-Benzaldehyde oxime (E-2g)

Mp 113−115 ℃; Rf = 0.4 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3461, 3156, 2923, 2854, 1639, 1433, 1351, 1268, 954, 850, 754, 691 cm−1; 1H NMR (300 MHz, CDCl3) : δ 7.36 (s, 1H), 7.39−7.47 (m, 3H), 7.91−7.97 (m, 2H), 8.35 (s, OH, D2O exchangeable); 13C NMR (75 MHz, CDCl3): δ 128.4, 130.1, 130.3, 130.8, 147.0; HRMS(EI): m/z calcd for C7H7NO: 121.0528; found: 121.0529.

(Z)-Benzaldehyde oxime (Z-2g)

Liquid; Rf = 0.57 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3388, 2896, 2771, 1954, 1895, 1692, 1634, 1497, 1449, 1292, 1211, 956, 869, 756 cm−1; 1H NMR (300 MHz, CDCl3) : δ 7.32−7.36 (m, 3H), 7.53−7.58 (m, 2H), 8.18 (s, 1H), 9.95 (s, OH, D2O exchangeable ); 13C NMR (75 MHz, CDCl3): δ 127.0, 128.7, 130.0, 131.6, 150.5; HRMS (EI): m/z calcd for C7H7NO: 121.0528; found: 121.0529.

(E)-4-Methoxybenzaldehyde oxime (E-2h)

Mp 84−85 ℃ (lit.22 74 ℃ ); Rf = 0.38 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3173, 3069, 3009, 2925, 2837, 2793, 1599, 1506, 1448, 1406, 1351, 1301, 1257, 1172, 1113, 1022, 951, 827, 743 cm−1; 1H NMR (300 MHz, CDCl3) : δ 3.83 (s, 3H), 6.90−6.96 (m, 2H), 7.31 (s, 1H), 7.92−7.96 (m, 2H), 8.98 (s, OH, D2O exchangeable); 13C NMR (75 MHz, CDCl3): δ 55.31, 113.7, 132.0, 132.4, 146.3, 160.6; HRMS (EI): m/z calcd for C8H9NO2: 151.0633; found: 151.0631.

(Z)-4-Methoxybenzaldehyde oxime (2h)

Mp 44−46 ℃; Rf = 0.43 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3301, 3005, 2963, 2937, 2910, 2838, 1607, 1575, 1515, 1463, 1418, 1304, 1252, 1109, 1029, 957, 874, 829 cm−1; 1H NMR (300 MHz, CDCl3) : δ 3.81 (s, 3H), 6.09 (d, 2H, J = 8.76 Hz), 7.51 (d, 2H, J = 8.7 Hz), 8.11 (s, 1H), 9.03 (s, OH, D2O exchangeable ); 13C NMR (75 MHz, CDCl3): δ 55.31, 114.2, 124.5, 128.5, 149.8, 161.0; HRMS (EI): m/z calcd for C8H9NO2: 151.0633; found: 151.0631.

(E)-2-Methylbenzaldehyde oxime (E-2i)

Mp 88−89 ℃; Rf = 0.28 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3191, 3086, 3030, 2987, 2866, 1656, 1600, 1437, 1328, 1275, 1260, 1217, 1037, 956, 939, 854, 764 cm−1; 1H NMR (300 MHz, CDCl3) : ℃ 2.39 (s, 3H), 7.22−7.32 (m, 3H), 7.64 (s, 1H), 7.88−7.92 (m, 1H), 8.41 (s, OH, D2O exchangeable); 13C NMR (75 MHz, , CDCl3): ℃ 19.88, 125.6, 129.2, 129.6, 129.7, 130.4, 136.8, 146.3; HRMS (EI): m/z calcd for C8H9NO: 135.0684; found: 135.0683.

(Z)-2-Methylbenzaldehyde oxime (Z-2i)

Mp 46−48 ℃; Rf = 0.43 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3317, 3069, 3022, 2984, 2922, 2779, 1622, 1489, 1457, 1433, 1312, 1292, 1226, 1125, 1034, 951, 871, 754, 716 cm−1; 1H NMR (300 MHz, CDCl3) : ℃ 2.38 (s, 3H), 7.14−7.28 (m, 3H), 7.65−7.68 (m, 1H), 8.44 (s, 1H), 9.72 (s, OH, D2O exchangeable). 13C NMR (75 MHz, CDCl3): ℃ 19.77, 126.3, 126.6, 130.0, 130.1, 130.9, 136.2, 149.3; HRMS (EI): m/z calcd for C8H9NO: 135.0684; found: 135.0683.

(E)-3-Bromobenzaldehyde oxime (E-2j)

Mp 98−100 ℃; Rf = 0.25 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3170, 3069, 2840, 2746, 1949, 1685, 1644, 1559, 1463, 1415, 1330, 1269, 1191, 1073, 955, 917, 900, 877, 780, 749 cm−1; 1H NMR (300 MHz, CDCl3) : ℃ 7.31−7.33 (m, 2H), 7.53−7.56 (m, 1H), 7.78−7.81 (m, 1H), 8.15−8.16 (m, 1H); 13C NMR (75 MHz, CDCl3): ℃ 129.3, 130.0, 133.1, 133.6, 145.4; HRMS (EI): m/z calcd for C7H6NOBr: 189.9633; found: 189.9635.

(Z)-3-Bromobenzaldehyde oxime (Z-2j)

Mp 57−59 ℃; Rf = 0.43 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3343, 3065, 2939, 2888, 2832, 2752, 1943, 1695, 1566, 1475, 1421, 1351, 1310, 1272, 1200, 1105, 1064, 976, 908, 875, 702 cm−1; 1H NMR (300 MHz, CDCl3) : ℃ 7.23−7.28 (m, 1H), 7.47−7.53 (m, 2H), 7.74−7.75 (m, 1H), 8.08 (s, 1H), 8.19 (s, OH, D2O exchangeable); 13C NMR (75 MHz, CDCl3): ℃ 125.6, 129.7, 130.2, 132.9, 149.0; HRMS(EI): m/z calcd for C7H6NOBr: 189.9633; found: 189.9635.

(E)-4-Nitrobenzaldehyde oxime (E-2k)

Mp 157−159 ℃ (lit.23 146 ℃); Rf = 0.31 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3180, 3067, 3014, 2926, 2880, 2837, 2788, 1601, 1519, 1441, 1401, 1344, 1318, 1264, 1192, 1104, 1013, 967, 942, 909, 852, 840, 746 cm−1; 1H NMR (300 MHz, DMSO-d6): δ 7.67 (s, 1H), 8.21−8.24 (m, 2H), 8.29−8.32 (m, 2H), 12.27 (s, OH, D2O exchangeable); 13C NMR (75 MHz, DMSO-d6): δ 123.6, 131.3, 136.2, 143.0, 147.0; HRMS (EI): m/z calcd for C7H6N2O3: 166.0378; found: 166.0378.

(Z)-4-Nitrobenzaldehyde oxime (Z-2k)

Mp 128−129 ℃ (lit24 129 ℃); Rf = 0.44 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3335, 3079, 2938, 1925, 1803, 1602, 1535, 1347, 1213, 1105, 969, 845, 746 cm−1; 1H NMR (300 MHz, DMSO-d6) : δ 7.85−7.89 (m, 2H), 8.24−8.28 (m, 2H), 8.32 (s, 1H), 11.89 (s, OH, D2O exchangeable); 13C NMR (75 MHz, DMSO-d6): δ 123.9, 127.2, 139.4, 146.7, 147.4; HRMS (EI): m/z calcd for C7H6N2O3: 166.0378; found: 166.0378.

(E)-4-Cyanobenzaldehyde oxime (E-2l)

Mp 138−140 ℃; Rf = 0.1 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3259, 2981, 2963, 2868, 2855, 2227, 1459, 1403, 1275, 1260, 1176, 1082, 916, 828, 763, 749, 704 cm−1; 1H NMR (300 MHz, DMSO-d6) : δ 7.58 (s, 1H), 7.74 (d, 2H, J = 8.19 Hz), 8.13 (d, 2H, J = 8.49 Hz), 12.15 (s, OH, D2O exchangeable ); 13C NMR (75 MHz, DMSO-d6): δ 111.5, 126.9, 130.7, 132.3, 132.6, 143.4; HRMS (EI): m/z calcd for C8H6N2O: 146.0480; found: 146.0478.

(Z)-4-Cyanobenzaldehyde oxime (Z-2l)

Mp 171−173 ℃; Rf = 0.2 (n-hexane : ethyl acetate = 3:1, v/v); IR (KBr): 3208, 3003, 2980, 2955, 2935, 2896, 2831, 2225, 1399, 1326, 1305, 1278, 1261, 1191, 1101, 1056, 971, 938, 873, 842, 824, 750, 702 cm−1; 1H NMR (300 MHz, DMSO-d6): δ 7.78 (d, 2H, J = 8.1 Hz), 7.87 (d, 2H, J = 8.1 Hz), 8.25 (s, 1H), 11.7 (s, OH, D2O exchangeable); 13C NMR (75 MHz, DMSO-d6): δ 111.2, 118.6, 126.9, 132.6, 137.5, 147.0; HRMS (EI): m/z calcd for C8H6N2O: 146.0480; found: 146.0478.

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