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

HRID 1110408Notes

Reaction equation

HRID 1110408 reaction equation
[Cr](Cl)([O-])(=O)=[O:2].[NH+]1C=CC=CC=1.[CH:12]1([C:15]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)(O)[CH:16]=[CH2:17])[CH2:14][CH2:13]1>C(Cl)Cl>[CH:12]1([C:15]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:16][CH:17]=[O:2])[CH2:14][CH2:13]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 51.3 grams (0.192 mole) of pyridinium chlorochromate in 210 mL of methylene chloride was added in one portion a solution of 20.0 grams (0.096 mole) of 1-cyclopropyl-1-(4-chlorophenyl)-2-propen-1-ol in 25 mL of methylene chloride. Upon completion of addition the reaction mixture was stirred at ambient temperature for two hours. The supernatent liquid was decanted from a residue, and the residue was extracted with diethyl ether. The decantate and the extract were combined and were washed in turn with two 100 mL portions of aqueous 5% hydrochloric acid, and a 50 mL portion 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 using 5% diethyl ether in hexane as the eluant. The appropriate fractions were combined and concentrated under reduced pressure yielding 6.8 grams of 3-cyclopropyl-3-(4-chlorophenyl)propenal.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. customThe supernatent liquid was decanted from a residue
  3. extractionthe residue was extracted with diethyl ether
  4. washwere washed in turn with two 100 mL portions of aqueous 5% hydrochloric acid
  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. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca605f17cf124dcd8befc0f1321ac99a
Source dataset
uspto-grants-1990_12
Patent number
US04975451

Reaction notes

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