(2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanone → 2-(Diethoxymethyl)-4,4-dimethylcyclohexanone
Reaction equation
O/C=[C:3]1/[C:4](=[O:11])[CH2:5][CH2:6][C:7]([CH3:10])([CH3:9])[CH2:8]/1.F[B-](F)(F)F.[CH2:17]([O:19][CH+:20][O:21][CH2:22][CH3:23])[CH3:18]>>[CH2:17]([O:19][CH:20]([O:21][CH2:22][CH3:23])[CH:3]1[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][CH2:5][C:4]1=[O:11])[CH3:18]Participants
Procedure
Another route involves reacting dimethylcyclohexanone (1A) with a prepared solution of diethoxycarbenium fluoroborate to provide 2-(diethoxymethyl)-4,4-dimethylcyclohexanone (8). The reaction is typically performed below room temperature in a solvent such as but not limited to methylene chloride. Chlorophenyl magnesium bromide is then added to a solution of 2-(diethoxymethyl)-4,4-dimethylcyclohexanone (8) to provide 1-(4-chlorophenyl)-2-(diethoxymethyl)-4,4-dimethylcyclohexanol (9). The reaction is typically performed below room temperature in a solvent such as but not limited to tetrahydrofuran. 1-(4-Chlorophenyl)-2-(diethoxymethyl)-4,4-dimethylcyclohexanol (9) can be treated with an acid such as but not limited to HCl, to provide the aldehyde intermediate (2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-ene-1-carbaldehyde) (4).
Sources & evidence
- ORD record
- ord-410958017f07431fbf4af5287f56bad4
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168784B2
Reaction notes
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