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

HRID 1015647Notes

Reaction equation

HRID 1015647 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-bc73a6d8800a435b871cd16af9b681e8
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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