Methacrylic Acid → HCID 59289097, compound

HRID 386338Notes

Reaction equation

HRID 386338 reaction equation
Br[CH2:2][C:3]([CH3:18])([CH3:17])[CH2:4][O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9]1)=[O:7].[C:19]([OH:24])(=[O:23])[C:20]([CH3:22])=[CH2:21].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:17][C:3]([CH3:18])([CH2:2][O:24][C:19](=[O:23])[C:20]([CH3:22])=[CH2:21])[CH2:4][O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 11430Potassium CarbonateHCID 592890294-Propyl-cyclohexanecarboxylic acid 3-bromo-2,2-dimethyl-propyl ester

Product 1

HCID 59289097HCID 59289097, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Propyl-cyclohexanecarboxylic acid 3-bromo-2,2-dimethyl-propyl ester (4.3 g, 13.3 mmol), methacrylic acid (3.4 g, 39.9 mmol) and potassium carbonate (6.9 g, 50.0 mmol) are stirred at 100° C. in dimethyl sulphoxide (100 ml) for 3d. 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 petrol as eluant to give 22 as a liquid.

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-8cbe1a62429743d181417fb5887de095
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Reaction notes

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