3-Cyclopropyl-3-(4-chlorophenyl)propan-1-ol → 3-Cyclopropyl-3-(4-chlorophenyl)propionaldehyde

HRID 1588877Notes

Reaction equation

HRID 1588877 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH:12]1([CH:15]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:16][CH2:17][OH:18])[CH2:14][CH2:13]1>C(Cl)Cl.C(OCC)C>[CH:12]1([CH:15]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:16][CH:17]=[O:18])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 197548323-Cyclopropyl-3-(4-chlorophenyl)propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 197548433-Cyclopropyl-3-(4-chlorophenyl)propionaldehydeYield 24%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6.5 grams (0.03 mole) of pyridinium chlorochromate in 25 ml of methylene chloride was stirred, and a solution of 2.1 grams (0.03 mole) of 3-cyclopropyl-3-(4-chlorophenyl)propan-1-ol in 5 ml of methylene chloride was quickly added. Upon completion of addition, the reaction mixture was stirred at ambient temperature for one hour. The reaction mixture was then diluted with 100 ml of diethyl ether, and this mixture was filtered through a pad of activated magnesium silicate. The filtrate was concentrated under reduced pressure, yielding 1.5 grams of 3-cyclopropyl-3-(4-chlorophenyl)propionaldehyde.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture was stirred at ambient temperature for one hour
  3. filtrationthis mixture was filtered through a pad of activated magnesium silicate
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e7b8daec8f9d4998aad5ea326c1e59dc
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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