Potassium Carbonate → HCID 86601708, compound

HRID 2220001Notes

Reaction equation

HRID 2220001 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:31])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]Br.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[Br:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:31])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 855511,11-DibromoundecaneHCID 19873709HCID 19873709, compound

Product 1

HCID 86601708HCID 86601708, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3.5 g (8.4 mmol) of 4-Octyloxy-benzoic acid (4′-hydroxy-biphenyl-4-yl) ester, 7.88 g (25 mmol) of 1,11-Dibromoundecane, 3.45 g (25 mmol) of K2CO3 and 50 mL of dry butanone is refluxed for 24 h, then allowed to return to room temperature. The reaction mixture is filtered off and the butanone is distilled off under reduced pressure. The crude product purified by column chromatography on silica gel using CH2Cl2 as eluent gives a pure product as a white solid (5.35 g, 85% yield).

Workup

  1. temperatureis refluxed for 24 h
  2. customto return to room temperature
  3. filtrationThe reaction mixture is filtered off
  4. distillationthe butanone is distilled off under reduced pressure
  5. customThe crude product purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0f01775aecfc4fdda92922b559ddb934
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

Loading…