Carbon Tetrachloride → HCID 13854292, compound

HRID 1194039Notes

Reaction equation

HRID 1194039 reaction equation
[CH3:1][C:2]([CH3:21])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)[CH:3]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:41](Cl)(Cl)([Cl:43])[Cl:42]>[Zn]>[CH3:1][C:2]([CH3:21])([CH:3]=[C:41]([Cl:43])[Cl:42])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 138494092,2-Dimethyl-3-[(3-phenoxyphenyl)methoxy]propanal

Product 1

HCID 13854292HCID 13854292, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A mixture of 2,2-dimethyl-3-(3-phenoxybenzyloxy)propan-1-al (0.25 g), triphenylphosphine (0.47 g), zinc dust (0.12 g) and carbon tetrachloride (0.2 cm3) was heated at the relux temperature for one hour. After cooling to the ambient temperature (ca 25° C.) 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 residual oil subjected to purification by flash chromatography using a silica gel column eluted with dichloromethane to yield 2,2-dimethyl-1-(3-phenoxybenzyloxy)-4,4-dichlorobut-3-ene (0.2 g).

Workup

  1. temperaturewas heated at the relux temperature for one hour
  2. customthe solid component removed by filtration
  3. concentrationThe filtrate was concentrated by evaporation of the solvent under reduced pressure
  4. customthe residual oil subjected to purification by flash chromatography
  5. washeluted with dichloromethane

Sources & evidence

ORD record
ord-602e7ad75ee34cc488bbf9973228aaa6
Source dataset
uspto-grants-1989_03
Patent number
US04812483

Reaction notes

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