Hydrochloric Acid → Cyclohexanone, 3,3-dimethyl-

HRID 1415721Notes

Reaction equation

HRID 1415721 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[CH3:9][Al](C)C.C[Si](Cl)(C)C.Cl>CCCCCC.C1COCC1>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 145113-Methyl-2-cyclohexen-1-oneHCID 16682925Trimethylaluminum

Product 1

HCID 76322Cyclohexanone, 3,3-dimethyl-Yield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

1.1 g (10 mmol) of 3-methyl-cyclohex-2-en-1-one and 28 mg (0.2 mmol) of CuBr are introduced into 15 ml of THF. 11 ml (11 mmol) of a 10% trimethylaluminum solution in hexane and 2.16 g (20 mmol) of trimethylsilyl chloride are added at 0° C. and stirred for 3 hours at room temperature. It is hydrolyzed with 10 ml of 1N hydrochloric acid, extracted with ethyl acetate, and the solvent is evaporated. 1.21 g (97% of theory) of 3,3-dimethylcyclohexanone is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-90562b32c69546c8b59b87c6da779f44
Source dataset
uspto-grants-1999_06
Patent number
US05908945

Reaction notes

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