Acrolein → HCID 23051268, compound

HRID 2232151Notes

Reaction equation

HRID 2232151 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N+]=[N-])=[CH:4][CH:3]=1.[CH:18]([CH:20]=[CH2:21])=[O:19]>ClCCl.CCCCCCC.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH2:21][CH:20]2[CH:18]=[O:19])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 7847AcroleinHCID 19781460HCID 19781460, compound

Product 1

HCID 23051268HCID 23051268, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of bis(4-fluorophenyl)diazomethane, prepared as in Example 84 from the action of activated manganese dioxide (59.7 g) on 4,4'-difluorobenzophenone hydrazone (42.81 g) in dichloromethane (195 mL), was added to a solution of acrolein (15.7 mL) in heptane (150 mL). The deep purple reaction mixture, after being stirred at 40° C. for 2 hours then at 53° C. for 30 minutes, faded to a pale amber color. Evaporation of the solvents afforded 46 g of 2,2-bis(4-fluorophenyl)cyclopropanecarboxaldehyde as an oil. The material was used without further purification in subsequent reactions.

Workup

  1. waitat 53° C. for 30 minutes
  2. customEvaporation of the solvents

Sources & evidence

ORD record
ord-4950fa8897b24035bfdcf0e431add6d1
Source dataset
uspto-grants-1988_11
Patent number
US04786646

Reaction notes

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