4-(4-Chlorophenyl)cyclohexane-1-carboxylic acid → [Trans-4-(4-chlorophenyl)cyclohexyl]methanol

HRID 1015377Notes

Reaction equation

HRID 1015377 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([C:14](O)=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][CH:11]([CH2:14][OH:15])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

Product 1

HCID 53925853[Trans-4-(4-chlorophenyl)cyclohexyl]methanolYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(4-Chlorophenyl)cyclohexane carboxylic acid (0.35 g, 1.5 mmol) was reacted via Method E over 72 hours. The solid was poured into a water (40 mL) solution and extracted with ethyl acetate (EtOAc) (4×10 mL). The combined organic layers were washed with brine (40 mL) and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo to obtain [4-(4-chlorophenyl)cyclohexyl]methanol (0.210 g, 64% yield).

Workup

  1. extractionextracted with ethyl acetate (EtOAc) (4×10 mL)
  2. washThe combined organic layers were washed with brine (40 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-d161dfce120c4e5d8e678822da9c3586
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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