Cyclopropyl methyl ketone → HCID 19558805, compound

HRID 351232Notes

Reaction equation

HRID 351232 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:19][C:20]([CH:22]1[CH2:24][CH2:23]1)=[O:21]>CCO.O>[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14](/[CH:15]=[CH:19]/[C:20]([CH:22]2[CH2:24][CH2:23]2)=[O:21])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 14798Sodium HydroxideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-

Product 1

HCID 19558805HCID 19558805, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

1M NaOH (4.8 ml) was added to a solution of 4-benzyloxybenzaldehyde (5 g) and cyclopropyl methyl ketone (3.96 g) in EtOH (24 ml) and the mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with H2O and EtOH. The mixture was stirred at ambient temperature for 20 minutes. Pale yellow crystals were collected and washed with H2O and 50% aqueous EtOH to give (2E)-3-[4-(benzyloxy)phenyl]-1-cyclopropyl-2-propen-1-one (6.29 g).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 20 minutes
  2. customPale yellow crystals were collected
  3. washwashed with H2O and 50% aqueous EtOH

Sources & evidence

ORD record
ord-76af6773b7564a34a42a7ead8b54e6aa
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

Loading…