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

HRID 1940309Notes

Reaction equation

HRID 1940309 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.[OH-].[Na+].C(O)(=O)C>O.C(O)C>[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

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 21187944Methyl 3-cyclopentyloxy-4-(methylthio)benzoate

Product 1

HCID 211878293-Cyclopentyloxy-4-(methylthio)benzoic acidYield 91.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of methyl 3-cyclopentyloxy-4-(methylthio)benzoate (24.3 g, 91.4 mmol) in water (200 mL) and ethanol (50 mL) containing sodium hydroxide (18.3 g, 460 mmol) is heated under reflux for 3 hours. The solution is then poured into water (750 mL) and 1N acetic acid is added dropwise with stirring to between pH 5-6.The solid which separates is collected by filtration, washed with water (4×100 mL) and dried giving 3-cyclopentyloxy-4-(methylthio)benzoic acid (21.1 g, 91.7%) as a cream solid m.p. 158°-160° C. [Elemental analysis: C,61.5; H,6.31%; calculated: C,61.88; H,6 39%]

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 (4×100 mL)
  6. customdried

Sources & evidence

ORD record
ord-c3bd32d0dea748dd8fbdddecf9c52b63
Source dataset
uspto-grants-1997_12
Patent number
US05698711

Reaction notes

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