Abstract
The hydrolysis of ${\alpha}$-bromophenylacetamide in the acidic media has been studied. The reactions in sulfuric acid and p-toluenesulfonic acid afforded mainly mandelic acid ; on the other hand, in hydrochloric acid ${\alpha}$-chlorophenylacetic acid was the main product. In either case, it was difficult to obtain ${\alpha}$-bromophenylacetic acid without concomittant formation of mandelic acid and ${\alpha}$-chlorophenylacetic acid respectively from the hydrolysis of ${\alpha}$-bromophenylacetamide. Mandelic acid and ${\alpha}$-chlorophenylacetic acid were obtained in good yields (86, 95 %) in sulfuric and hydrochloric acid respectively; the reactions are therefore potentially useful processes for obtaining them.
${\alpha}$-Bromophenylacetamide를 황산중에서 가수분해시키면 대개의 경우 mandelic acid와 ${\alpha}$-bromophenylacetic acid의 혼합물이 얻어지고, 염산의 경우에는 ${\alpha}$-chlorophenylacetic acid만이 얻어졌다. 그러나 조건을 잘 조절하면 mandelic acid와 ${\alpha}$-chlorophenylacetic acid는 각각 86, 95 % 이상의 좋은 수율로 순수하게 생성되지만, ${\alpha}$-bromophenylacetic acid만을 순수하게 생성시키는 최적 조건은 찾지 못하였다. 즉 이들 조건에서 ${\alpha}$-탄소의 브롬이 각각 $OH^{\Theta}$ 와 $Cl^{\Theta}$로 쉽게 치환되었다.