Potassium Carbonate → 4'-(10-Bromodecyloxy)biphenyl-4-carboxylic acid ethyl ester

HRID 231026Notes

Reaction equation

HRID 231026 reaction equation
[CH2:1]([O:3][C:4]([C:6]1(O)[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH2:7]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]Br.C(=O)([O-])[O-:32].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:32][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][Br:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2214831,10-DibromodecaneHCID 68717694HCID 68717694, compound

Product 1

HCID 539849124'-(10-Bromodecyloxy)biphenyl-4-carboxylic acid ethyl esterYield 72.6%

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(45.0 g) of 1,10-dibromodecane, 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 29.9 g of 4'-(10-bromodecyloxy)biphenyl-4-carboxylic acid ethyl ester. (yield: 72%)

Workup

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

Sources & evidence

ORD record
ord-513924bdea1b410eac7bc5195855043b
Source dataset
uspto-grants-1989_07
Patent number
US04844835

Reaction notes

Loading…