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

HRID 14310

Reaction equation

HRID 14310 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-0a58eacd02b5468d880f03d8c475fcf6
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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