Potassium Carbonate → 4-[4-(11-Bromo-undecyloxy)-phenyl]-cyclohexanol

HRID 2220003Notes

Reaction equation

HRID 2220003 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH:5]2[CH2:4][CH2:3][CH:2]([OH:1])[CH2:7][CH2:6]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 855511,11-DibromoundecaneHCID 101764984-(cis-4-Hydroxycyclohexyl)phenol

Product 1

HCID 179809754-[4-(11-Bromo-undecyloxy)-phenyl]-cyclohexanolYield 85%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2.40 g (0.012 mol) of 4-(4-Hydroxy-cyclohexyl)-phenol obtained in Step 1, 11.76 (0.037 mol) of 1,11-Dibromoundecane, 5.17 g (0.037 mol) of K2CO3 and 40 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 is purified by recrystallisation from ethanol to give a pure product as a white solid (4.34 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 is purified by recrystallisation from ethanol

Sources & evidence

ORD record
ord-1f8b331ecbaa47a8af0068c7531042e7
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

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