p-Toluenesulfonic acid → 4-Propyl-cyclohexanecarboxylic acid 3-bromo-2,2-dimethyl-propyl ester

HRID 386337

반응식

HRID 386337 반응식
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Br:13][CH2:14][C:15]([CH3:19])([CH3:18])[CH2:16]O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:13][CH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][O:11][C:10]([CH:7]1[CH2:8][CH2:9][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]1)=[O:12]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 1425013-Bromo-2,2-dimethyl-1-propanolHCID 1490324(1s,4r)-4-Propylcyclohexane-1-carboxylic acid

생성물 1

HCID 592890294-Propyl-cyclohexanecarboxylic acid 3-bromo-2,2-dimethyl-propyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

4-Propyl-cyclohexanecarboxylic acid (10.0 g, 58.0 mmol), 3-bromo-2,2-dimethyl-propan-1-ol (10.0 g, 59.9 mmol) and a catalytic amount of para-toluene sulphonic acid are stirred under reflux in toluene (300 ml) in a flask equipped with Dean-Stark apparatus over night. The solution is allowed to cool to room temperature, is washed with aqueous sodium carbonate and water, dried and evaporated to dryness. Purification is achieved by filtration through a silica pad using petrol as eluant. Evaporation of the appropriate fractions gives 4-propyl-cyclohexanecarboxylic acid 3-bromo-2,2-dimethyl-propyl ester as a liquid. The structure is confirmed by GCMS.

후처리

  1. customequipped with Dean-Stark apparatus over night
  2. washis washed with aqueous sodium carbonate and water
  3. customdried
  4. customevaporated to dryness
  5. customPurification
  6. filtrationis achieved by filtration through a silica pad
  7. customEvaporation of the appropriate fractions

출처 및 근거

ORD 기록
ord-cd78500ab0584a6ebb5131e7949cf338
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372307B2

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