Potassium Carbonate → HCID 58047395, compound

HRID 1888746Notes

Reaction equation

HRID 1888746 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:12][CH:13]1[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:12][CH:13]2[CH2:15][CH2:14]2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 1853632-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 58047395HCID 58047395, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-chloro-4-hydroxybenzaldehyde (1.00 g, 6.39 mmol), bromomethylcyclopropane (0.93 mL, 9.58 mmol) and potassium carbonate (1.77 g, 12.8 mmol) in DMF (8 mL) was stirred under heating at 50° C. for 1 day. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 3:1) to give the title compound (1.08 g, yield 80%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 3:1)

Sources & evidence

ORD record
ord-f6c120ea5d344a40bcbfa5a0e2522e81
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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