Diethyl Ether → 3-(2,4-Dichlorophenyl)-2-(4-chlorophenyl)propanal

HRID 488588Notes

Reaction equation

HRID 488588 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH2:11][OH:12].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)[CH:11]=[O:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12391212HCID 12391212, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 222703593-(2,4-Dichlorophenyl)-2-(4-chlorophenyl)propanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2,4-dichlorophenyl)-2-(4-chorophenyl)propanol (Step B, 0.89 g, 2.8 mmol) in 20 mL CH2Cl2 was added crushed activated molecular sieves (4 g). After stirring at room temperature for 10 min, pyridinium chlorochromate (0.90 g, 4.2 mmol) was added. After stirring at room temperature for 1 h, CELITE diatomaceous earth (4 g) was added followed by 100 mL ether. The resulting mixture was filtered through a silica gel pad, which was washed with ether (2×50 mL). The filtrate was concentrated to dryness and azeotroped with toluene to give the title compound, which was used without further purification.

Workup

  1. customcrushed activated molecular sieves (4 g)
  2. stirringAfter stirring at room temperature for 1 h
  3. additionCELITE diatomaceous earth (4 g) was added
  4. filtrationThe resulting mixture was filtered through a silica gel pad, which
  5. washwas washed with ether (2×50 mL)
  6. concentrationThe filtrate was concentrated to dryness
  7. customazeotroped with toluene

Sources & evidence

ORD record
ord-e078a4c74ded4d5c8fd96bd8382beba0
Source dataset
uspto-grants-2005_12
Patent number
US06972295B2

Reaction notes

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