Potassium Carbonate → 3-Cyclopentyloxy-4-(methylthio)benzoic acid

HRID 1584933Notes

Reaction equation

HRID 1584933 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[S:17][CH3:18])[C:10]([O:12]C)=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[S:17][CH3:18])[C:10]([OH:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 21187944Methyl 3-cyclopentyloxy-4-(methylthio)benzoate

Product 1

HCID 211878293-Cyclopentyloxy-4-(methylthio)benzoic acidYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of methyl 3-cyclopentyloxy-4-(methylthio)benzoate (0.8 g) in methanol (10 mL) and water (5 mL) is treated with potassium carbonate (0.48 g) and the mixture is heated at reflux for 7 hours. The mixture is concentrated, and the resulting residue is partitioned between diethyl ether (20 mL) and water (20 mL). The aqueous layer is separated, acidified to pH 1 by treatment with dilute hydrochloric acid (2N), and extracted with dichloromethane (2×25 mL). The combined organic extracts are dried and concentrated, to give 3-cyclopentyloxy-4-(methylthio)benzoic acid (0.7 g) in the form of a white solid m.p. 150-152° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 7 hours
  3. concentrationThe mixture is concentrated
  4. customthe resulting residue is partitioned between diethyl ether (20 mL) and water (20 mL)
  5. customThe aqueous layer is separated
  6. extractionextracted with dichloromethane (2×25 mL)
  7. customThe combined organic extracts are dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e9bd568e32584ad1b79806d0150ec2c8
Source dataset
uspto-grants-1999_08
Patent number
US05935978

Reaction notes

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