Water → 4-Cyanophenylvinyl cyclopropyl ketone

HRID 359791Notes

Reaction equation

HRID 359791 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[CH3:11][C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13].[OH-].[Na+].O>C(O)C>[CH:14]1([C:12]([CH:11]=[CH:7][C:6]2[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[O:13])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 13004Cyclopropyl methyl ketoneHCID 14798Sodium HydroxideHCID 660424-Cyanobenzaldehyde

Product 1

HCID 572526194-Cyanophenylvinyl cyclopropyl ketoneYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 39.3 g of 4-cyanobenzaldehyde and 25.2 g of cyclopropyl methyl ketone in 60 ml of absolute ethanol was added 21 ml of 20% sodium hydroxide solution over a 25 minute period. The mixture was stirred for one hour at room temperature, cooled to 1° C. and 40 ml of cold water added. The solid material was collected by filtration and triturated with 450 ml of methylene dichloride and 150 ml of water at room temperature. The aqueous phase was extracted with methylene dichloride and the combined organic layers dried and concentrated in vacuo. The residue was recrystallized from absolute ethanol to give 45.0 g of 4-cyanophenylvinyl cyclopropyl ketone, m.p. 104° C.

Workup

  1. temperaturecooled to 1° C.
  2. filtrationThe solid material was collected by filtration
  3. customtriturated with 450 ml of methylene dichloride and 150 ml of water at room temperature
  4. extractionThe aqueous phase was extracted with methylene dichloride
  5. customthe combined organic layers dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-60571564ce674ae28f3912915a4bfc08
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

Loading…