Potassium Carbonate → HCID 23157404, compound

HRID 507993Notes

Reaction equation

HRID 507993 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][CH:13]([CH3:15])[CH3:14].[C:16]1([CH:22](Br)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:16]1([CH:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[CH2:12][CH:13]([CH3:15])[CH3:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 19080443HCID 19080443, compound

Product 1

HCID 23157404HCID 23157404, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-hydroxy-3-isobutylbenzoate (0.80 g, 3.84 mmol), diphenylmethyl bromide (1.05 g, 4.25 mmol) and potassium carbonate (0.69 g, 4.99 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 3 days. The reaction solution was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed with aqueous citric acid solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate/hexane=3/97-15/85) to give the title compound (450 mg, yield 31%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with aqueous citric acid solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3132497045204f8d91f3e36863834bea
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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