Dimethyl 1,4-cyclohexanedicarboxylate → 4-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

HRID 1197324Notes

Reaction equation

HRID 1197324 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-].[K+]>CO>[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 7198Dimethyl 1,4-cyclohexanedicarboxylateHCID 14797Potassium Hydroxide

Product 1

HCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acidYield 33.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of dimethyl 1, 4-cyclohexane-dicarboxylate (20 g, Aldrich) in methanol (50 ml) was added a solution of potassium hydroxide (7.3 g) in methanol (75 ml). The reaction mixture was refluxed for 16 hours. After cooling the solvent was removed on a rotary evaporator. The residue was taken up in ether and water and extracted to remove unreacted starting diester. The aqueous layer was acidified with dilute hydrochloric acid and re-extracted with ether. The ether extracts were washed with brine and dried. Evaporation in vacuo gave a solid. Purification was achieved by recrystallization from ethyl acetate to yield 4-methoxycarbonylcyclohexanecarboxylic acid (6.2 g), m.pt 90.9° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. temperatureAfter cooling the solvent
  3. customwas removed on a rotary evaporator
  4. extractionwater and extracted
  5. customto remove unreacted
  6. extractionre-extracted with ether
  7. washThe ether extracts were washed with brine
  8. customdried
  9. customEvaporation in vacuo
  10. customgave a solid
  11. customPurification
  12. customwas achieved by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-aa1a4ef9ce8343f5830770e4d8a6c45b
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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