تفاعل #55649

معادلة التفاعل

3-[(4-methoxyphenyl)methyl]glutaric acid

ethanethiol

→

3-[(4-hydroxyphenyl)methyl]glutaric acid

المردود 79.4%

المذيبات

dimethylformamide

dimethylformamide

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىevaporated in vacuo
2. 2
   استخلاصextracted with ether
3. 3
   استخلاصextracted with ethyl acetate
4. 4
   غسيلwashed once with brine
5. 5
   أخرىdried
6. 6
   أخرىevaporated
7. 7
   أخرىthe residue crystallized from a mixture of ethyl acetate-chloroform-hexane

الإجراء التجريبي

To a stirred suspension of 57% sodium hydride-paraffin (1.4 g) in dry dimethylformamide (30 ml) is added dropwise a solution of ethanethiol (4.0 ml) in dry dimethylformamide (10 ml). After 15 minutes, a solution of 3-[(4-methoxyphenyl)methyl]glutaric acid (800 mg) in dry dimethylformamide (20 ml) is added. The resulting slurry is heated in a bath at 165° C. for 20 hours and evaporated in vacuo. The residue is acidified with 20% hydrochloric acid, extracted with ether and the extracts are discarded. The aqueous solution is saturated with salt and extracted with ethyl acetate. The extracts are combined, washed once with brine, dried, evaporated and the residue crystallized from a mixture of ethyl acetate-chloroform-hexane to give 600 mg of 3-[(4-hydroxyphenyl)methyl]glutaric acid, melting point 117°-119° C.

المصدر