Carbon Tetrachloride → HCID 13854290, compound

HRID 1194038Notes

Reaction equation

HRID 1194038 reaction equation
[CH3:1][C:2]([CH3:22])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)[CH:3]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42](Cl)(Cl)([Cl:44])[Cl:43]>>[CH3:1][C:2]([CH3:22])([CH:3]=[C:42]([Cl:44])[Cl:43])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 13849410HCID 13849410, compound

Product 1

HCID 13854290HCID 13854290, compound

Procedure

A mixture of 2,2-dimethyl-3-(4-fluoro-3-phenoxybenzyloxy)propan-1-al (0.5 g), triphenylphosphine (0.43 g) and carbon tetrachloride (1.0 cm3) was heated at the reflux temperature for 1 hour. After cooling to the ambient temperature the mixture was diluted with petroleum ether (boiling range 40°-60° C.) and the solid component removed by filtration. The filtrate was concentrated by evaporation of the solvent under reduced pressure and the redidual oil subjected to purification by flash chromatography using a silica column eluted with petroleum ether (boiling range 40°-60° C.) containing diethyl ether (10% by volume) as eluent to yield 2,2-dimethyl-1-(4-fluoro-3-phenoxybenzyloxy)-4,4-dichlorbut-3-ene (0.1 g) as a colourless oil.

Workup

  1. temperaturewas heated at the reflux temperature for 1 hour
  2. customthe solid component removed by filtration
  3. concentrationThe filtrate was concentrated by evaporation of the solvent under reduced pressure
  4. customthe redidual oil subjected to purification by flash chromatography
  5. washeluted with petroleum ether (boiling range 40°-60° C.)
  6. additioncontaining diethyl ether (10% by volume) as eluent

Sources & evidence

ORD record
ord-38d2978da83d432790c1284dff1711fa
Source dataset
uspto-grants-1989_03
Patent number
US04812483

Reaction notes

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