Lithium Hydroxide → 4-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

HRID 349099

Reaction equation

HRID 349099 reaction equation
[CH:1]1([C:11]([O:13]C)=[O:12])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.[OH-].[Li+]>O1CCCC1.CO.O>[CH3:10][O:9][C:7]([CH:4]1[CH2:5][CH2:6][CH:1]([C:11]([OH:13])=[O:12])[CH2:2][CH2:3]1)=[O:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 7198Dimethyl 1,4-cyclohexanedicarboxylate

Product 1

HCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acidYield 77.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of dimethyl cyclohexane-1,4-dicarboxylate (10.2 g, 51 mmol) in a mixture of 2:1:1 tetrahydrofuran/methanol/water (52 mL) was added lithium hydroxide (2.13 g, 51 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was partitioned between diethyl ether and water. The aqueous layer was acidified to pH 4 with 1 N hydrochloric acid, and the precipitate collected, and dried under vacuum to afford 4-(methoxycarbonyl)cyclohexanecarboxylic acid (7.4 g): 1H NMR (300 MHz, CDCl3) δ 3.68 (s, 3H), 2.33–2.27 (m, 2H), 2.11–2.06 (m, 4H), 1.50–1.43 (m, 4H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between diethyl ether and water
  3. customthe precipitate collected
  4. customdried under vacuum

Sources & evidence

ORD record
ord-43304f0fdc8f4b1eb1d65be76a622463
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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