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

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Reaction Steps

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(CDC13)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.

Provenance & Evidence