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

HRID 904075

反応式

HRID 904075 の反応式
[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

参加物

5

反応物 3

HCID 6343EthanethiolHCID 5360545SodiumHCID 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 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.

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-b32488a21b1d4ff4b7be8e0489eea5e3
出典データセット
uspto-grants-1980_10
特許番号
US04230621

関連ノート

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