Dihydro-beta-ionone → Dihydro-beta-ionol
Reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[CH2:10][CH2:11][C:12]([CH3:14])=[O:13].[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1[CH2:10][CH2:11][CH:12]([OH:13])[CH3:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dihydro-beta-ionone (J. Am. Chem. Soc., 108, 7314 (1986)) is reduced with sodium borohydride in ethanol in the usual fashion to provide 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanol as a colorless oil. This is coupled with 4-hydroxybenzaldehyde by the method of example 13, and the resulting aldehyde is chain-extended and condensed with glyoxylic acid by the methods of example 1. The title compound is obtained as a colorless solid, mp 99°-101° after recrystallization from hexane-chloroform
Sources & evidence
- ORD record
- ord-6ac473605cb2492bb8532de5d2c2a815
- Source dataset
- uspto-grants-1995_11
- Patent number
- US05464865
Reaction notes
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