Sodium Hydroxide → 4-[3-[3-Hydroxy-4-(methoxycarbonyl)-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid

HRID 2225832Notes

Reaction equation

HRID 2225832 reaction equation
C([O:3][C:4](=[O:32])[C:5](=[O:31])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([OH:27])[C:18]=2[CH2:28][CH2:29][CH3:30])=[CH:8][CH:7]=1)C.[OH-].[Na+]>CO>[OH:27][C:19]1[C:18]([CH2:28][CH2:29][CH3:30])=[C:17]([CH:22]=[CH:21][C:20]=1[C:23]([O:25][CH3:26])=[O:24])[O:16][CH2:15][CH2:14][CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([C:5](=[O:31])[C:4]([OH:32])=[O:3])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 678299744-[3-[3-Hydroxy-4-(methoxycarbonyl)-2-propylphenoxy) propoxy]-alpha-oxobenzeneacetic acid ethyl ester

Product 1

HCID 190044424-[3-[3-Hydroxy-4-(methoxycarbonyl)-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acidYield 58.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in Example 19, a solution of 4-[3-[3-hydroxy-4-(methoxycarbonyl)-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.3 g) in methanol (30 mL) was treated with 4N sodium hydroxide (0.53 mL) and then was stirred at room temperature for 1 hour. Most of the solvents were removed in vacuo, then the mixture was acidified with 3N hydrochloric acid and extracted with ethyl acetate. The dried (MgSO4) extracts were evaporated and the crude acid was crystallized from a carbon tetrachloride-hexane mixture containing a small amount of dichloromethane to yield 0.164 g of 4-[3-[3-hydroxy-4-(methoxycarbonyl)-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid, as a colorless solid, mp 86°-87° C.

Workup

  1. customMost of the solvents were removed in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialThe dried (MgSO4) extracts
  4. customwere evaporated
  5. customthe crude acid was crystallized from a carbon tetrachloride-hexane mixture
  6. additioncontaining a small amount of dichloromethane

Sources & evidence

ORD record
ord-4357bd1ae5c8411e8e06b12f04ebd48b
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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