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

HRID 1613066Notes

Reaction equation

HRID 1613066 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:40])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([OH:39])[CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:30][O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([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:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 88068Methyl 3-HydroxybenzoateHCID 149862851-(6-Iodohexyl)-2,3-bis(phenylmethoxy)benzene

Product 1

HCID 149863463-[6-[2,3-Bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid methyl esterYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.58 g of 1-(6-iodohexyl)-2,3-bis (phenylmethoxy)benzene, 0.18 g of 3-hydroxybenzoic acid methyl ester and 0.25 g of potassium carbonate in 15 mL of acetone was stirred at reflux for 18 hours. Workup as in Example 16 and purification by HPLC using toluene gave 0.40 g (66% yield) of 3-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 18 hours
  2. customWorkup as in Example 16 and purification by HPLC

Sources & evidence

ORD record
ord-f3ae2a24b7e94cc19dc719bf3c7d7361
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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