1-(4-Chlorophenyl)-1-cyclopropyl-2-propen-1-ol → HCID 57191402, compound

HRID 1383226Notes

Reaction equation

HRID 1383226 reaction equation
[Cr](Cl)([O-])(=O)=[O:2].[NH+]1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:23]2[CH2:25][CH2:24]2)(O)[CH:20]=[CH2:21])=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:23]2[CH2:25][CH2:24]2)=[CH:20][CH:21]=[O:2])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 150420331-(4-Chlorophenyl)-1-cyclopropyl-2-propen-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 57191402HCID 57191402, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 40.3 grams (0.192 mole) of pyridinium chlorochromate in 210 mL of methylene chloride was added a solution of 20.0 grams (0.096 mole) of 1-(4-chlorophenyl)-1-cyclopropyl-2-propen-1-ol in 25 mL of methylene chloride in one portion. Upon completion of addition, the reaction mixture was stirred for two hours. A supernatent layer was decanted from a residue, and the residue was extracted with diethyl ether. The supernatent layer was combined with the ether extracts, and the combination was washed with two 100 mL portions of an aqueous 5% sodium hydroxide solution, 100 mL of an aqueous 5% hydrochloric acid solution, and then with 50 mL of an aqueous solution saturated with sodium bicarbonate. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 5% diethyl ether in hexane. The appropriate fractions were combined and concentrated under reduced pressure, yielding 6.8 grams of 3-(4-chlorophenyl)-3-cyclopropylpropenal.

Workup

  1. additionUpon completion of addition
  2. customA supernatent layer was decanted from a residue
  3. extractionthe residue was extracted with diethyl ether
  4. washthe combination was washed with two 100 mL portions of an aqueous 5% sodium hydroxide solution, 100 mL of an aqueous 5% hydrochloric acid solution
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. washElution
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0dfcf1920a74385b523eea6d4a4a975
Source dataset
uspto-grants-1989_02
Patent number
US04808762

Reaction notes

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