Gamma-Butyrolactone → 4-((3-Bromophenyl)thio)butanoic acid

HRID 37415

반응식

HRID 37415 반응식
[Na].[Br:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[C:10]1(=[O:15])[O:14][CH2:13][CH2:12][CH2:11]1>C(O)C>[Br:2][C:3]1[CH:4]=[C:5]([S:9][CH2:13][CH2:12][CH2:11][C:10]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 7302Gamma-ButyrolactoneHCID 80597m-BromobenzenethiolHCID 5360545Sodium

생성물 1

HCID 545154194-((3-Bromophenyl)thio)butanoic acid

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
110 °C

실험 절차

3.74 g of sodium were dissolved in 77 ml of absolute ethanol under argon. The solution was treated dropwise with 25 g of m-bromothiophenol and heated to reflux. Thereafter, 12.4 ml of γ-butyrolactone were added and the reaction mixture was heated to 110° C. for 5 hours. The separated carboxylic acid sodium salt was removed by filtration, washed with a small amount of ether and dissolved in 300 ml of water. The solution was acidified to pH 2 with 1N HCl while cooling with ice, the free carboxylic acid was extracted with ether, the ethereal solution was dried and evaporated. There were obtained 33.1 g of 4-(m-bromophenylmercapto)butyric acid.

후처리

  1. temperatureheated to reflux
  2. customThe separated carboxylic acid sodium salt was removed by filtration
  3. washwashed with a small amount of ether
  4. dissolutiondissolved in 300 ml of water
  5. temperaturewhile cooling with ice
  6. extractionthe free carboxylic acid was extracted with ether
  7. customthe ethereal solution was dried
  8. customevaporated

출처 및 근거

ORD 기록
ord-6cb72450fdfa4b8d8d6fea27607b02ae
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420273

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