Methanol → Methyl trans-4-(4-chlorophenyl)cyclohexanecarboxylate

HRID 1506375Notes

Reaction equation

HRID 1506375 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:17]O>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][CH:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

Product 1

HCID 14794634Methyl trans-4-(4-chlorophenyl)cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a stirred solution of the 4-(4-chlorophenyl)cyclohexanecarboxylic acid (0.5 g, 2.095 mmol) in methanol (10 mL) was added one drop of conc. sulfuric acid. After stirring overnight at room temperature, the reaction mixture was extracted with ethyl acetate and washed with water, saturated sodium bicarbonate and brine. It was then dried over anhyd. magnesium sulfate, concentrated and dried in vacuo to yield methyl 4-(4-chlorophenyl)cyclohexanecarboxylate a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.23-7.30 (2H, m), 7.10-7.17 (2H, m), 3.70 (3H, s), 2.44-2.56 (1H, m), 2.36 (1H, tt, J=12.13, 3.60 Hz), 2.07-2.16 (2H, m), 1.92-2.01 (2H, m), 1.38-1.67 (4H, m).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water, saturated sodium bicarbonate and brine
  3. customIt was then dried over anhyd
  4. concentrationmagnesium sulfate, concentrated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-11325f44eee54b93abea31128109bdbd
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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