Potassium Carbonate → HCID 17980976, compound

HRID 2220011Notes

Reaction equation

HRID 2220011 reaction equation
[CH2:1]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][Br:38].C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[Br:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])=[CH:14][CH:15]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 855511,11-DibromoundecaneHCID 17980978HCID 17980978, compound

Product 1

HCID 17980976HCID 17980976, compoundYield 183.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2.80 g (8.68 mmol) of the compound obtained in Step 1, 8.18 g (26.0 mmol) of 1,11-Dibromo-undecane, 3.66 g ((26.0 mmol) of K2CO3 and 40 mL of dry butanone is refluxed for 24 h, then the reaction mixture is allowed to return to room temperature. The mixture is filtered and the solvent is distilled off under reduced pressure. The resulting crude is purified by column chromatography on silica gel using CH2Cl2 as eluent to give a pure white solid (9.11 g, 41% yield).

Workup

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

Sources & evidence

ORD record
ord-b543593afdbd466cba9db1243ea8ba8a
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

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