Ethanethiol → 3-[(4-Hydroxyphenyl)methyl]glutaric acid

HRID 904075

반응식

HRID 904075 반응식
[Na].C(S)C.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH2:19][C:20]([OH:22])=[O:21])[CH2:15][C:16]([OH:18])=[O:17])=[CH:9][CH:8]=1>CN(C)C=O>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH2:19][C:20]([OH:22])=[O:21])[CH2:15][C:16]([OH:18])=[O:17])=[CH:9][CH:8]=1

참가 물질

5

반응물 3

HCID 6343EthanethiolHCID 5360545SodiumHCID 205288313-[(4-Methoxyphenyl)methyl]glutaric acid

생성물 1

HCID 205288373-[(4-Hydroxyphenyl)methyl]glutaric acid수율 79.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

반응 조건

온도
165 °C

실험 절차

To a stirred suspension of 57% sodium hydrideparaffin (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.

후처리

  1. customevaporated in vacuo
  2. extractionextracted with ether
  3. extractionextracted with ethyl acetate
  4. washwashed once with brine
  5. customdried
  6. customevaporated
  7. customthe residue crystallized from a mixture of ethyl acetate-chloroform-hexane

출처 및 근거

ORD 기록
ord-b32488a21b1d4ff4b7be8e0489eea5e3
출처 데이터셋
uspto-grants-1980_10
특허 번호
US04230621

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