Acetic Acid → 3-Cyclopentyloxy-4-(methylthio)benzoic acid

HRID 1870378Notes

Reaction equation

HRID 1870378 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:18]=[CH:19][C:20]=2[S:21][CH3:22])[C:10]([O:12]C2CCCC2)=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].C(O)(=O)C>O.CO>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:18]=[CH:19][C:20]=2[S:21][CH3:22])[C:10]([OH:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 21187855Cyclopentyl 3-cyclopentyloxy-4-(methylthio)benzoate

Product 1

HCID 211878293-Cyclopentyloxy-4-(methylthio)benzoic acidYield 92.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of cyclopentyl 3-cyclopentyloxy-4-(methylthio)benzoate (0.5 g, 1.5 mmol) in water (30 mL) and methanol (10 mL) containing sodium hydroxide (1 g, 25 mmol) is heated under reflux for 3 hours. The solution is then poured into water (60 mL) and acetic acid is added dropwise with stirring to between pH 5-6. The solid which separates is collected by filtration, washed with water (5×10 mL) and dried giving 3-cyclopentyloxy-4-(methylthio)benzoic acid (0.35 g, 88.6%) as a cream solid m.p. 158-160° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. additionis added dropwise
  4. filtrationThe solid which separates is collected by filtration
  5. washwashed with water (5×10 mL)
  6. customdried

Sources & evidence

ORD record
ord-f24e02b5225a4debbf201cb59add979a
Source dataset
uspto-grants-2000_08
Patent number
US06096768

Reaction notes

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