4-[3-(3,4-Dimethoxyphenyl)propoxy]-2-hydroxy-3-propylbenzoic acid methyl ester → 4-[3-(3,4-Dimethoxyphenyl)propoxy]-2-hydroxy-3-propylbenzoic acid

HRID 1613069Notes

Reaction equation

HRID 1613069 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27]>CO.[OH-].[Na+]>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([CH2:13][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:28])=[O:2])=[C:5]([OH:27])[C:6]=2[CH2:24][CH2:25][CH3:26])[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

4

Reactant 1

HCID 149863534-[3-(3,4-Dimethoxyphenyl)propoxy]-2-hydroxy-3-propylbenzoic acid methyl ester

Product 1

HCID 149863574-[3-(3,4-Dimethoxyphenyl)propoxy]-2-hydroxy-3-propylbenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 7.1 g of 4-[3-(3,4-dimethoxyphenyl)propoxy]-2-hydroxy-3-propylbenzoic acid methyl ester in 180 mL of methanol and 90 mL of 1N sodium hydroxide was stirred at reflux for 1 hour. The solvent was removed under reduced pressure, the residue was acidified and the product was extracted with methylene chloride. The dried (MgSO4) extract was concentrated to 6.5 g, mp 104°-110°, of 4-[3-(3,4-dimethoxyphenyl)propoxy]-2-hydroxy-3-propylbenzoic acid.

Workup

  1. temperatureat reflux for 1 hour
  2. customThe solvent was removed under reduced pressure
  3. extractionthe product was extracted with methylene chloride
  4. dry with materialThe dried (MgSO4)
  5. extractionextract
  6. concentrationwas concentrated to 6.5 g, mp 104°-110°, of 4-[3-(3,4-dimethoxyphenyl)propoxy]-2-hydroxy-3-propylbenzoic acid

Sources & evidence

ORD record
ord-11671b1f3d7b45d681850fffef5d2fa2
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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