Potassium Carbonate → 4'-(12-Bromododecyloxy)biphenyl-4-carboxylic acid ethyl ester

HRID 2082187Notes

Reaction equation

HRID 2082187 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]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][CH2:31][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 187661,12-DibromododecaneHCID 4049156Ethyl 4'-hydroxy-4-biphenylcarboxylate

Product 1

HCID 539084014'-(12-Bromododecyloxy)biphenyl-4-carboxylic acid ethyl esterYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An acetone solution of 90 m moles (21.8 g) of the above 4'-hydroxybiphenyl-4-carboxylic acid ethyl ester, 0.15 mole (49.2 g) of 1,12-dibromododecane, 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 29.5 g of 4'-(12-bromododecyloxy)biphenyl-4-carboxylic acid ethyl ester [m.p. 88.6°-90.5° C⟧ (yield: 67%)

Workup

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

Sources & evidence

ORD record
ord-74eae7d364954a5b909c4151f237dbf1
Source dataset
uspto-grants-1993_02
Patent number
US05187298

Reaction notes

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