HCID 15233467, compound → HCID 15233468, compound

HRID 1492846Notes

Reaction equation

HRID 1492846 reaction equation
[CH3:1][O:2][C:3](=[O:48])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]CC3C=CC=CC=3)=[CH:17][CH:16]=2)[CH:7]=[C:6]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:5]=1.[H][H]>[Pd].C1COCC1>[CH3:1][O:2][C:3](=[O:48])[C:4]1[CH:5]=[C:6]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:7]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 15233467HCID 15233467, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15233468HCID 15233468, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.40 g of 3-(octadecyloxy)-5-[3-[4-(phenylmethoxy) phenoxy]propoxy]benzoic acid methyl ester and 0.1 g of 10% palladium on carbon in 25 ml of THF was stirred in a hydrogen atmosphere for 4 hours. The usual workup followed by purification by chromatography on 12 g of silica gel (230-400 mesh) using 20% ethyl acetate-hexane to give 0.177 g (51% yield, mp 85°-88°) of 3-[3-(4-hydroxyphenoxy)propoxy]-5-(octadecyloxy)benzoic acid methyl ester.

Workup

  1. customThe usual workup followed by purification by chromatography on 12 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-abb087305042402cb4638e4c67024fd6
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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