α-Ethyl-2,4,6-trimethyl-3-cyclohexene-1-methanol → 1-(2,4,6-Trimethyl-cyclohex-3-enyl)-propan-1-one

HRID 61323Notes

Reaction equation

[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH2:5][CH:4]([CH3:9])[CH:3]1[CH:10]([OH:13])[CH2:11][CH3:12]>CC(C)=O.S(=O)(=O)(O)O.O.[O-2].[O-2].[O-2].[Cr+6]>[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH2:5][CH:4]([CH3:9])[CH:3]1[C:10](=[O:13])[CH2:11][CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(2,4,6-Trimethyl-cyclohex-3-enyl)-propan-1-ol (182 g, 1.0 mol) dissolved in acetone (400 mL) was added dropwise to a solution of chromium trioxide (CrO3, 108 g, 1.08 mol) in aqueous sulfuric acid (H2SO4, 400 mL, 172 g in water) at −10° C. The resulting mixture was aged for 2 hours as the mixture warmed to 0° C. The mixture was then diluted with water and extracted with toluene. The organic layer was concentrated by rotary evaporation and distilled via fractionation to provide 1-(2,4,6-trimethyl-cyclohex-3-enyl)-propan-1-one (113 g, 63% yield) as a colorless liquid.

Workup

extractionextracted with toluene
concentrationThe organic layer was concentrated by rotary evaporation
distillationdistilled via fractionation

Sources & evidence

ORD record: ord-6c49ac40a28a43b58cd0798446b1487d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09441185B2

Reaction notes

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