HCID 10899886, compound → 3-(3-Methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-one

HRID 2247801Notes

Reaction equation

HRID 2247801 reaction equation
[CH3:1][O:2][C:3]([CH3:15])([CH3:14])[CH2:4][CH2:5][CH:6]1[CH2:11][C:10]([CH3:12])=[CH:9][C:8](=[O:13])[CH2:7]1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3]([CH3:14])([CH3:15])[CH2:4][CH2:5][CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][C:8](=[O:13])[CH2:7]1

Participants

5

Reactant 2

HCID 10899886HCID 10899886, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 147939943-(3-Methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohex-5-en-1-one (30.0 g, 0.14 mol) in methanol (150 mL) was placed in a thick walled bottle. Palladium on charcoal (5%, 2.0 g) was added and the mixture was shaken under 53.5 psi of hydrogen. When the theoretical amount of hydrogen had been consumed, workup yielded 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-one as a mixture of two diastereoisomers bp0.5 104-107~C. (27.6 g, ratio 69:93.1); NMR(CDCl3)δ1.0(d,3H), 1.1(s,6H), 1.3-1.5(m,6H), 1.6-2.0(m,4H), 2.2-2.4(m,2H),3.1(s,3H). IR(neat) 2970, 2925, 1720, 1360, 1090 cm-1 ; MS(m/e) 41, 73, 124, 147, 165, 180, 197.

Workup

  1. customWhen the theoretical amount of hydrogen had been consumed

Sources & evidence

ORD record
ord-5677bb345ab142fa84cdfcc840077ac2
Source dataset
uspto-grants-1991_08
Patent number
US05037802

Reaction notes

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