Potassium Carbonate → HCID 22926256, compound

HRID 1985283Notes

Reaction equation

HRID 1985283 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:15][CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[CH2:18]([O:17][CH2:16][CH2:15][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[CH:12][CH:11]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 143274-CyclohexylphenolHCID 73833Benzene, ((2-bromoethoxy)methyl)-

Product 1

HCID 22926256HCID 22926256, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 2.5 g of 4-cyclohexylphenol, 3.0 g of benzyl 2-bromoethyl ether and 2.4 g of potassium carbonate in N,N-dimethylformamide (50 ml) was stirred at 60° C. for 23 hours. The reaction solution was diluted with water and ethyl acetate. The organic layer was washed with saturated aqueous potassium carbonate and saturated ammonium chloride (×2), dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography, to give 3.9 g of the title compound as a colorless oil.

Workup

  1. washThe organic layer was washed with saturated aqueous potassium carbonate and saturated ammonium chloride (×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5423f5f435cc4961995a92f4e9602dd9
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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