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

HRID 27371

反応式

HRID 27371 の反応式
C(S)C.C[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH2:18][C:19]([OH:21])=[O:20])[CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=1>CN(C)C=O>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH2:18][C:19]([OH:21])=[O:20])[CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=1

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
165 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-033aa82002814349b96762619854d38d
出典データセット
uspto-grants-1980_09
特許番号
US04221725

関連ノート

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