Sodium Hydroxide → 4-(3-Methanesulfonyl-phenoxy)-benzoic acid

HRID 552581Notes

Reaction equation

HRID 552581 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO.O1CCCC1>[CH3:20][S:17]([C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[CH:5][CH:6]=1)(=[O:18])=[O:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 671652314-(3-Methanesulfonyl-phenoxy)-benzoic acid methyl ester2×

Product 1

HCID 438071184-(3-Methanesulfonyl-phenoxy)-benzoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A stirred solution of 4-(3-methanesulfonyl-phenoxy)-benzoic acid methyl ester (1.0 mmol) (see Intermediate 12) in 1:1 methanol/tetrahydrofuran (0.15 M), is treated with 2 N sodium hydroxide (3.0 mmol) and heated to reflux for one hour. The reaction is concentrated in vacuo. 1 N Hydrochloric acid and water are added and the mixture extracted with 10% isopropanol/dichloromethane. The organic portion is concentrated in vacuo to yield the desired product. MS (m/e): 291.0 (M−1).

Workup

  1. temperatureheated
  2. temperatureto reflux for one hour
  3. concentrationThe reaction is concentrated in vacuo
  4. addition1 N Hydrochloric acid and water are added
  5. extractionthe mixture extracted with 10% isopropanol/dichloromethane
  6. concentrationThe organic portion is concentrated in vacuo

Sources & evidence

ORD record
ord-b5a64fae860540e3bccdde31c0487644
Source dataset
uspto-grants-2011_05
Patent number
US07951826B2

Reaction notes

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