Phosphorus trichloride → Benzene, 1,1′-[1-(chloromethyl)-1,2-ethenediyl]bis-

HRID 597139Notes

Reaction equation

HRID 597139 reaction equation
[C:1]1([CH:7](O)[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)[Cl:18]>C(Cl)Cl>[C:10]1([C:8](=[CH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][Cl:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 11586526HCID 11586526, compound

Product 1

HCID 54379748Benzene, 1,1′-[1-(chloromethyl)-1,2-ethenediyl]bis-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution comprised of 14 parts of 1,2-diphenyl-2-propen-1-ol and 24.3 parts of methylene chloride is added dropwise to a solution comprised of 12.6 parts of phosphorous trichloride and 30.4 parts of methylene chloride at a temperature of -15°. That reaction mixture is allowed to warm to 0° over a 3 hour period. Then ice is added while stirring rapidly and the oil which separates is extracted with ethyl ether. The ethereal extracts are washed with water and then with 10% potassium bicarbonate solution. After drying over anhydrous sodium sulfate, the solution is reduced to an oil by evaporating the solvent under a nitrogen stream and reduced pressure to yield pure 2,3-diphenylallyl chloride.

Workup

  1. additionis added dropwise to a solution
  2. temperatureto warm to 0° over a 3 hour period
  3. additionThen ice is added
  4. extractionthe oil which separates is extracted with ethyl ether
  5. washThe ethereal extracts are washed with water
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customby evaporating the solvent under a nitrogen stream and reduced pressure

Sources & evidence

ORD record
ord-aa6e6d45da8d44929a40ccc54a08c3b3
Source dataset
uspto-grants-1977_03
Patent number
US04013643

Reaction notes

Loading…