Dichloromethane → 1-(4-Chlorophenyl)-2-(diethoxymethyl)-4,4-dimethylcyclohexanol

HRID 1920478Notes

Reaction equation

HRID 1920478 reaction equation
Cl[Mg][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br-].[CH2:10]([O:12][CH:13]([O:23][CH2:24][CH3:25])[CH:14]1[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][CH2:16][C:15]1=[O:22])[CH3:11].C(Cl)[Cl:27]>>[Cl:27][C:3]1[CH:8]=[CH:7][C:6]([C:15]2([OH:22])[CH2:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH2:19][CH:14]2[CH:13]([O:12][CH2:10][CH3:11])[O:23][CH2:24][CH3:25])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 580183412-(Diethoxymethyl)-4,4-dimethylcyclohexanoneHCID 178419578HCID 178419578, compound

Product 1

HCID 580183391-(4-Chlorophenyl)-2-(diethoxymethyl)-4,4-dimethylcyclohexanol

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).

Workup

  1. customis typically performed below room temperature in a solvent

Sources & evidence

ORD record
ord-dc34e7ae38174a269a32df5ba7e33f2c
Source dataset
uspto-grants-2012_05
Patent number
US08168784B2

Reaction notes

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