Sodium Hydroxide → 4-[3-[4-Carboxy-3-hydroxy-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid

HRID 2225833Notes

Reaction equation

HRID 2225833 reaction equation
[OH:1][C:2]1[C:3]([CH2:28][CH2:29][CH3:30])=[C:4]([CH:21]=[CH:22][C:23]=1[C:24]([O:26]C)=[O:25])[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:20])[C:17]([OH:19])=[O:18])=[CH:12][CH:11]=1.[OH-].[Na+]>CO>[C:24]([C:23]1[CH:22]=[CH:21][C:4]([O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:20])[C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)=[C:3]([CH2:28][CH2:29][CH3:30])[C:2]=1[OH:1])([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 190044424-[3-[3-Hydroxy-4-(methoxycarbonyl)-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid

Product 1

HCID 190044864-[3-[4-Carboxy-3-hydroxy-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[3-[3-hydroxy-4-(methoxycarbonyl)-2-propylphenoxy)propoxy]-alphaoxobenzeneacetic acid (0.3 g) in methanol (30 mL) was treated with 4N sodium hydroxide (0.58 mL) was stirred at reflux for 46 hours. The methanol was removed in vacuo, then the mixture was acidified with 3N hydrochloric acid and extracted with dichloromethane-tetrahydrofuran (1:1). The dried (MgSO4) extracts were evaporated and the solid residue was crystallized from dichloromethane-hexane, and then from acetone-hexane to afford 4-[3-[4-carboxy-3-hydroxy-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid, mp 182°-185° C.

Workup

  1. temperatureat reflux for 46 hours
  2. customThe methanol was removed in vacuo
  3. extractionextracted with dichloromethane-tetrahydrofuran (1:1)
  4. dry with materialThe dried (MgSO4) extracts
  5. customwere evaporated
  6. customthe solid residue was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-a54f42d2d8fd4dbaa6deb86e846a3d40
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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