3,3-Bis(4-fluorophenyl)-2-(1-methylethyl)-propenol → 3-Methyl-2-bis(4-fluorophenyl)methylidenbutanal

HRID 1086063Notes

Reaction equation

HRID 1086063 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:9]([CH:12]([CH3:14])[CH3:13])=[CH:10][OH:11])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)=[C:9]([CH:12]([CH3:14])[CH3:13])[CH:10]=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 678945923,3-Bis(4-fluorophenyl)-2-(1-methylethyl)-propenolHCID 178418287HCID 178418287, compound

Product 1

HCID 140335263-Methyl-2-bis(4-fluorophenyl)methylidenbutanalYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3,3-bis(4-fluorophenyl)-2-(1-methylethyl)-propenol (2.0 g, 6.9 mmol) and pyridinium chlorochromate (3 g) in 100 mL dichloromethane was stirred for 20 hrs. during which time a dark gummy solid separated. The solvent was decanted from the solid and concentrated in vacuo. The residue was extracted with hexane and the hexane solution concentrated in vacuo. The residue was crystallized from petroleum ether to give 1.4 g of the title compound; m.p. =78°-84° C.

Workup

  1. customduring which time a dark gummy solid separated
  2. customThe solvent was decanted from the solid
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with hexane
  5. concentrationthe hexane solution concentrated in vacuo
  6. customThe residue was crystallized from petroleum ether

Sources & evidence

ORD record
ord-a2c98f8fe85f48548578f83a8b24119c
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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