Potassium Carbonate → 2-Hydroxy-5-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid methyl ester

HRID 1494234Notes

Reaction equation

HRID 1494234 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[C:37]([OH:39])[CH:36]=[CH:35][C:34]=1[OH:40].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[C:37]([O:39][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:36]=[CH:35][C:34]=1[OH:40]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75077Methyl GentisateHCID 149862851-(6-Iodohexyl)-2,3-bis(phenylmethoxy)benzene

Product 1

HCID 149863412-Hydroxy-5-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid methyl esterYield 39%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.00 g of 1-(6-iodohexyl)-2,3-bis(phenylmethoxy)benzene, 0.34 g of 2,5-dihydroxybenzoic acid methyl ester and 1.0 g of potassium carbonate in 30 mL of acetone was stirred at reflux for 17 hours. Workup as in Example 16 and chromatography on 60 g of silica gel using 1% ethyl acetate-toluene gave 0.42 g (39% yield) of 2-hydroxy-5-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 17 hours

Sources & evidence

ORD record
ord-140d0631289940a48d00e2df498ac064
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

Loading…