Methacrylic Acid → 4-Propyl-cyclohexanecarboxylic acid 4-(2-methyl-acryloyloxy)-butyl ester

HRID 386336Notes

Reaction equation

HRID 386336 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10]1)=[O:8].[C:18]([OH:23])(=[O:22])[C:19]([CH3:21])=[CH2:20].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:21][C:19](=[CH2:20])[C:18]([O:23][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10]1)=[O:8])=[O:22]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 11430Potassium CarbonateHCID 592890684-Propyl-cyclohexanecarboxylic acid 4-bromo-butyl ester

Product 1

HCID 592890634-Propyl-cyclohexanecarboxylic acid 4-(2-methyl-acryloyloxy)-butyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Propyl-cyclohexanecarboxylic acid 4-bromo-butyl ester (9.4 g, 30.8 mmol), methacrylic acid (8.0 g, 92.4 mmol) and potassium carbonate (17.0 g, 123.2 mmol) are stirred at 50° C. in dimethyl sulphoxide (200 ml) over night. A solid precipitate is removed by filtration and washed with diethyl ether. The filtrate is washed with water, removed, dried and evaporated to dryness. Purification is achieved by flash column chromatography using toluene as eluant to give 21 as an oil.

Workup

  1. customA solid precipitate is removed by filtration
  2. washwashed with diethyl ether
  3. washThe filtrate is washed with water
  4. customremoved
  5. customdried
  6. customevaporated to dryness
  7. customPurification

Sources & evidence

ORD record
ord-2cd387e8af354111aaf8d57e39a0cf24
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Reaction notes

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