4-[4-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]butanoic acid ethyl ester → 4-[4-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]butanoic acid

HRID 2231453Notes

Reaction equation

HRID 2231453 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25]([OH:32])[C:24]=2[CH2:33][CH2:34][CH3:35])[C:10]=1[CH2:36][CH2:37][CH3:38])C>CO.[OH-].[Na+]>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:39])=[O:3])=[C:10]([CH2:36][CH2:37][CH3:38])[C:11]=1[O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25]([OH:32])[C:24]=1[CH2:33][CH2:34][CH3:35])(=[O:17])[CH3:16]

Participants

4

Reactant 1

HCID 156230254-[4-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]butanoic acid ethyl ester

Product 1

HCID 133891564-[4-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]butanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 6.22 g of 4-[4-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]butanoic acid ethyl ester in 100 ml of methanol and 57 ml of 1N sodium hydroxide was stirred at reflux for 2 hours. The solvent was removed in vacuo and the pH of the residue was adjusted to 2.0 with 6N hydrochloric acid. The solid was filtered and dried to give 5.16 g (87%), mp 96°-99°, 4-[4-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]butanoic acid.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed in vacuo
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-104f080a781a4aef9e8bd83592c43e9b
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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