Calcium Carbonate → (4S,5R)-5-Methyl-4-(prop-2-en-1-yl)cyclohex-2-en-1-one

HRID 1650067Notes

Reaction equation

HRID 1650067 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH:5](SC2C=CC=CC=2)[CH2:4][CH:3]1[CH2:16][CH:17]=[CH2:18].C(=O)([O-])[O-].[Ca+2].S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[CH3:1][C@@H:2]1[CH2:7][C:6](=[O:8])[CH:5]=[CH:4][C@H:3]1[CH2:16][CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 198553365-Methyl-4-(2-propenyl)-2-phenylsulfenylcyclohexanone

Product 1

HCID 70359932(4S,5R)-5-Methyl-4-(prop-2-en-1-yl)cyclohex-2-en-1-oneYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 96.7 nmole of 5-methyl-4-(2-propenyl)-2-phenylsulfenylcyclohexanone and 10 g. (100 mmole) of calcium carbonate in 300 ml. of toluene was heated at 110° C. for 40 minutes. The reaction was cooled, magnesium sulfate added and filtered. The filtrate was evaporated and the residue purified via column chromatography on 300 g. of silica gel eluted with 20% ether-hexane and then distillation to yield 7.61 g. (52%) of the title compound.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue purified via column chromatography on 300 g
  5. washof silica gel eluted with 20% ether-hexane
  6. distillationdistillation
  7. customto yield 7.61 g

Sources & evidence

ORD record
ord-8d1432bbbd054d599a33842c6502562b
Source dataset
uspto-grants-1990_05
Patent number
US04921994

Reaction notes

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