Water → 3-Cyclopentyloxy-4-(methylthio)benzoic acid

HRID 356949Notes

Reaction equation

HRID 356949 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.O.C(=O)([O-])[O-].[K+].[K+]>CO>[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 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 21187944Methyl 3-cyclopentyloxy-4-(methylthio)benzoate

Product 1

HCID 211878293-Cyclopentyloxy-4-(methylthio)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of methyl 3-cyclopentyloxy-4-(methylthio)benzoate (0.8 g; that is prepared as described in Reference Example 54) 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 (2 N), 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. customthat is prepared
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 7 hours
  4. concentrationThe mixture is concentrated
  5. customthe resulting residue is partitioned between diethyl ether (20 mL) and water (20 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with dichloromethane (2×25 mL)
  8. customThe combined organic extracts are dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3d6cf4c6bd4247f2b9abc62a9e7f655e
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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