Sodium Hydroxide → 3-Methyl-cyclopent-3-enecarboxylic acid

HRID 2193931Notes

Reaction equation

HRID 2193931 reaction equation
C([O:3][C:4]([CH:6]1[CH2:10][CH:9]=[C:8]([CH3:11])[CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[CH3:11][C:8]1[CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 274458Ethyl 3-methylcyclopent-3-ene-1-carboxylate

Product 1

HCID 125754193-Methyl-cyclopent-3-enecarboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the 3-Methyl-cyclopent-3-enecarboxylic acid ethyl ester (255 mg, 1.65 mmol) in MeOH (4.0 mL) and 10% aq. NaOH (3.3 mL, 8.25 mmol) was heated at 50° C. for 16 h, reaction mixture was cooled to room temperature, solvent was evaporated, diluted with water. The aqueous solution was washed with ether, and acidified with aq. 1 N HCl, extracted with ether. The ethereal solution was washed with brine and dried. Evaporation of the solvent furnished the 3-Methyl-cyclopent-3-enecarboxylic acid (200 mg, 97% yield). 1H NMR (CDCl3, 400 MHz) 5.27 (brs, 1H), 3.26-3.17 (m, 1H), 2.7-2.55 (m, 4H), 1.74 (s, 3H).

Workup

  1. customreaction mixture
  2. customsolvent was evaporated
  3. additiondiluted with water
  4. washThe aqueous solution was washed with ether
  5. extractionextracted with ether
  6. washThe ethereal solution was washed with brine
  7. customdried
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d5219435675e4c75b3b72698e50ac2f6
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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