Potassium Carbonate → HCID 14986349, compound

HRID 1613067Notes

Reaction equation

HRID 1613067 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]=[CH:37][C:36]([OH:39])=[C:35]([Cl:40])[CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][C:36]([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)=[C:35]([Cl:40])[CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 149862851-(6-Iodohexyl)-2,3-bis(phenylmethoxy)benzene

Product 1

HCID 14986349HCID 14986349, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.6 g of 1-(6-iodohexyl)-2,3-bis(phenylmethoxy)benzene, 2.1 g of 3-chloro-4-hydroxybenzoic acid methyl ester and 5.0 g of potassium carbonate in 50 mL of acetone was stirred at reflux for 20 hours. Workup as in Example 16, chromatography on 100 g of silica gel using 15% ethyl acetate-hexane and crystallization from ethyl acetate-hexane gave 3.7 g (59% yield), mp 68°-69°, 3-chloro-4-[6-[2,3-bis (phenylmethoxy)phenyl]hexyloxy]benzoic acid methyl ester.

Workup

  1. temperatureat reflux for 20 hours
  2. customWorkup as in Example 16, chromatography on 100 g of silica gel using 15% ethyl acetate-hexane and crystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-cf8a941a827047c586c5e3cab55e41ea
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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