Potassium Carbonate → HCID 18954847, compound

HRID 2380656Notes

Reaction equation

HRID 2380656 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:16])[C:11](=[CH:14][CH:15]=1)[CH:12]=[O:13].Br[CH2:18][C:19]([CH:21]([CH3:23])[CH3:22])=[CH2:20]>CN(C)C=O>[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([O:16][CH2:20][C:19](=[CH2:18])[CH:21]([CH3:23])[CH3:22])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5201014-Chloro-2-hydroxybenzaldehydeHCID 112866351-Butene, 2-(bromomethyl)-3-methyl-

Product 1

HCID 18954847HCID 18954847, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 8.8 g (0.064 mol) of potassium carbonate in 100 mL of dimethylformamide was added 10.0 g (0.064 mol) of 4-chlorosalicylaldehyde and 12.5 g (0.077 mol) of 2-(bromomethyl)-3-methyl-1-butene. The reaction mixture was heated at 70° C. for 2 hours, cooled to room temperature and poured into 600 mL ice/water. The crude mixture was extracted with ethyl acetate (3×100 mL). The ethyl acetate was washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford 14.0 g of a yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe crude mixture was extracted with ethyl acetate (3×100 mL)
  3. washThe ethyl acetate was washed with water (100 mL) and brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff4b4fbddb2046bbb3c2838185cf95ca
Source dataset
uspto-grants-1994_11
Patent number
US05369121

Reaction notes

Loading…