Dimethyl Sulfate → HCID 66955155, compound

HRID 385237Notes

Reaction equation

HRID 385237 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[CH2:12][C:13]([CH:15]1[CH2:20][C:19](=[CH2:21])[CH2:18][CH2:17][CH:16]1[C:22]([OH:24])=[O:23])=[O:14])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O.C(OCC)(=O)C>[CH2:10]([C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[CH2:12][C:13]([CH:15]1[CH2:20][C:19](=[CH2:21])[CH2:18][CH2:17][CH:16]1[C:22]([O:24][CH3:25])=[O:23])=[O:14])[CH3:11]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 66954696HCID 66954696, compound

Product 1

HCID 66955155HCID 66955155, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.45 g (17.33 mmol) of 2-[(2,6-diethyl-4-methylphenyl)acetyl]-4-methylidenecyclohexane-carboxylic acid (XIII-1), together with 2.38 g of potassium carbonate and 2.62 g (20.8 mmol) of dimethylsulphate, are boiled at reflux in 50 ml of acetone for 5 h, and after cooling, the reaction mixture is taken up in ethyl acetate, extracted with water and dried (magnesium sulphate), and the solvent is distilled off. Chromatography on silica gel using ethyl acetate/hexane (v/v=30:70) gives 3.93 g (69%) of methyl 2-[(2,6-diethyl-4-methylphenyl)acetyl]-4-methylidenecyclohexane-carboxylate of the formula (II-1).

Workup

  1. temperatureafter cooling
  2. extractionextracted with water
  3. dry with materialdried (magnesium sulphate)
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-e04728493ddb4a4cbb56742342732e98
Source dataset
uspto-grants-2013_02
Patent number
US08367873B2

Reaction notes

Loading…