p-Toluenesulfonic acid → 4-Propyl-cyclohexanecarboxylic acid 4-acryloyloxy-butyl ester

HRID 386334

Reaction equation

HRID 386334 reaction equation
[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].[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21]O)(=[O:16])[CH:14]=[CH2:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][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])(=[O:16])[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 755884-Hydroxybutyl acrylateHCID 1490324(1s,4r)-4-Propylcyclohexane-1-carboxylic acid

Product 1

HCID 592890904-Propyl-cyclohexanecarboxylic acid 4-acryloyloxy-butyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Propyl-cyclohexanecarboxylic acid (10.0 g, 58.0 mmol), 4-hydroxybutyl acrylate (8.0 g, 57.0 mmol) and a catalytic amount of para-toluene sulphonic acid are stirred under reflux in toluene (100 ml) in a flask equipped with Dean-Stark apparatus. The reaction is shown to be complete by GCMS after 1 hour. 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 flash column chromatography using petrol as eluant. Evaporation of the appropriate fractions gives a colourless oil.

Workup

  1. customequipped with Dean-Stark apparatus
  2. washis washed with aqueous sodium carbonate and water
  3. customdried
  4. customevaporated to dryness
  5. customPurification
  6. customEvaporation of the appropriate fractions
  7. customgives a colourless oil

Sources & evidence

ORD record
ord-a2e30c497dba4744a6945527d75788a1
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Linked notes

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