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

HRID 1492866Notes

Reaction equation

HRID 1492866 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34]CC3C=CC=CC=3)[C:29]=2[O:42]CC2C=CC=CC=2)[CH:20]=1)[C:15]([OH:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H][H]>[Pd].C1COCC1>[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[C:29]=2[OH:42])[CH:20]=1)[C:15]([OH:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 189515713-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 189515483-(Decyloxy)-5-[[6-(2,3-dihydroxyphenyl)hexyl]oxy]benzoic acidYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.7 g of 3-(decyloxy)-5-[[6-[2,3-bis(phenylmethoxy) phenyl]hexyl]oxy]benzoic acid and 0.3 g of 10% palladium on carbon in 75 ml of THF was stirred in a hydrogen atmosphere until uptake ceased after 2.5 hours. The usual workup followed by trituration of the crude product from hexane and filtration gave 1.13 g (91% yield, mp 86°-88°) of 3-(decyloxy)-5-[[6-(2,3-dihydroxyphenyl)hexyl]oxy]benzoic acid.

Workup

  1. filtrationThe usual workup followed by trituration of the crude product from hexane and filtration

Sources & evidence

ORD record
ord-4d75744e6d434bbdb433974fdc7deddb
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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