Potassium Carbonate → 4'-(16-Bromohexadecyloxy)biphenyl-4-carboxylic acid ethyl ester

HRID 2072645Notes

Reaction equation

HRID 2072645 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][Br:19])=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5211771,16-DibromohexadecaneHCID 4049156Ethyl 4'-hydroxy-4-biphenylcarboxylate

Product 1

HCID 540173084'-(16-Bromohexadecyloxy)biphenyl-4-carboxylic acid ethyl esterYield 70.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An acetone solution of 90 m moles (21.8 g) of 4'-hydroxybiphenyl-4-carboxylic acid ethyl ester obtained in Example 24, 0.15 mole (57.6 g) of 1,16-dibromohexadecane, and 0.4 mole (55.3 g) of potassium carbonate was refluxed for four hours. The reaction solution was filtered. The filtrate was concentrated, and then purified by column chromatography to obtain 34.4 g of 4'-(16-bromohexadecyloxy)biphenyl-4-carboxylic acid ethyl ester. (yield: 70%)

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-bfd26be44c3a48b8a6e06b474ffb5c20
Source dataset
uspto-grants-1990_04
Patent number
US04913839

Reaction notes

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