Benzyl Bromide → 5-[[6-([1,1'-Biphenyl]-4-yloxy)hexyl]oxy]-2-(phenylmethoxy)benzoic acid methyl ester

HRID 488323Notes

Reaction equation

HRID 488323 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH:7]=[CH:6][C:5]=1[OH:30].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:22][CH:23]=2)[CH:7]=[CH:6][C:5]=1[O:30][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 545134655-[[6-([1,1'-Biphenyl]-4-yloxy) hexyl]oxy]-2-hydroxybenzoic acid methyl ester

Product 1

HCID 540228055-[[6-([1,1'-Biphenyl]-4-yloxy)hexyl]oxy]-2-(phenylmethoxy)benzoic acid methyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.4 g (3.3 mmol) of 5-[[6-([1,1'-biphenyl]-4-yloxy) hexyl]oxy]-2-hydroxybenzoic acid methyl ester, 0.6 ml (5 mmol) of benzyl bromide and 2.5 g (16.5 mmol) of potassium carbonate in 50 ml of acetone and 5 ml of DMF was stirred at reflux for 24 hours. After the usual workup, the crude product was recrystallized from ethyl acetate-hexane to give 1.5 g (89% yield, mp 85°-87°) of 5-[[6-([1,1'-biphenyl]-4-yloxy)hexyl]oxy]-2-(phenylmethoxy)benzoic acid methyl ester.

Workup

  1. temperatureat reflux for 24 hours
  2. customAfter the usual workup, the crude product was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-818d8a2844b34520ae6da3a62e890ef0
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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