3-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid methyl ester → 3-(Decyloxy)-5-[[6-(2,3-dihydroxyphenyl) hexyl]oxy]benzoic acid methyl ester

HRID 1492864Notes

Reaction equation

HRID 1492864 reaction equation
[CH3:1][O:2][C:3](=[O:50])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]CC3C=CC=CC=3)[C:18]=2[O:31]CC2C=CC=CC=2)[CH:7]=[C:6]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:5]=1.[H][H]>[Pd]>[CH3:1][O:2][C:3](=[O:50])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[C:18]=2[OH:31])[CH:7]=[C:6]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:5]=1

Participants

4

Reactant 2

HCID 538284933-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 537070423-(Decyloxy)-5-[[6-(2,3-dihydroxyphenyl) hexyl]oxy]benzoic acid methyl esterYield 87.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 0.7 g of 3-(decyloxy)-5-[[6-[2,3-bis(phenylmethoxy) phenyl]hexyl]oxy]benzoic acid methyl ester and 0.3 g of 10% palladium on carbon was stirred in a hydrogen atmosphere until uptake ceased after 4.5 hours. After the usual workup, the crude product was triturated with hexane and filtered to give 0.45 g (87% yield, mp 71°-72°) of 3-(decyloxy)-5-[[6-(2,3-dihydroxyphenyl) hexyl]oxy]benzoic acid methyl ester.

Workup

  1. customAfter the usual workup, the crude product was triturated with hexane
  2. filtrationfiltered

Sources & evidence

ORD record
ord-2f0a16b4dbe848fab6620b35ce471fdb
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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