4-[6-[2,3-Bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid ethyl ester → 4-[6-(2,3-Dihydroxyphenyl)hexyloxy]benzoic acid ethyl ester

HRID 1613090Notes

Reaction equation

HRID 1613090 reaction equation
[CH2:1]([O:3][C:4](=[O:40])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24]CC3C=CC=CC=3)[C:19]=2[O:32]CC2C=CC=CC=2)=[CH:7][CH:6]=1)[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:40])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[C:19]=2[OH:32])=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 149864454-[6-[2,3-Bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 149864464-[6-(2,3-Dihydroxyphenyl)hexyloxy]benzoic acid ethyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.3 g of 4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid ethyl ester in 50 mL of ethyl acetate and 0.3 g of 10% palladium on carbon was stirred in a hydrogen atmosphere for 22 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to a solid. Recrystallization from ethyl acetate-hexane gave 1.3 g, mp 45°-47°, (85% yield) to 4-[6-(2,3-dihydroxyphenyl)hexyloxy]benzoic acid ethyl ester.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure to a solid
  3. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e4fa265a00d549c7b54f0aa91cd2202d
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

Loading…