Cornforth reagent → HCID 11008833, compound

HRID 462879Notes

Reaction equation

HRID 462879 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:13])[CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[CH2:13])[CH2:9][CH2:10][CH:11]=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 132358184-(4-Chlorophenyl)pent-4-en-1-ol

Product 1

HCID 11008833HCID 11008833, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-chlorophenyl)pent-4-en-1-ol (5.5 g) and pyridinium dichromate (14.62 g) in dichloromethane (50 ml) was stirred at room temperature for 24 hours. The mixture was diluted with diethyl ether and the solid material was filtered off. The filtrate was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give 4-(4-chlorophenyl)pent-4-enal (2.6 g, 48%) as a yellow oil, 1H nmr (CDCl3): 9.75 (1H, broad singlet, CHO), 1R (film): 1720 cm-1.

Workup

  1. filtrationthe solid material was filtered off
  2. washThe filtrate was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58a61a90ce3b43cb8dfa614ac9b36038
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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