Phosphorus trichloride → 1-Chloro-1-(p-prenylphenyl)ethane
Reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:12](O)[CH3:13])=[CH:8][CH:7]=1)[CH:2]=[C:3]([CH3:5])[CH3:4].P(Cl)(Cl)[Cl:16]>CC(C)=O.N1C=CC=CC=1>[Cl:16][CH:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:1][CH:2]=[C:3]([CH3:5])[CH3:4])=[CH:7][CH:8]=1)[CH3:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
166 g of 1-(p-prenylphenyl)ethanol was dissolved in a mixture of 870 ml of acetone and 34.5 g of pyridine. While the solution was maintained at 0° C., 60.1 of phosphorus trichloride was added over the course of about 2 hours. The mixture was stirred at room temperature for 2 hours. Acetone was distilled off, and n-hexane and cold water were added to the mixture. The n-hexane layer was washed successively with a 1.6% aqueous solution of sodium hydroxide and water, dried and concentrated to give 174.6 g of 1-chloro-1-(p-prenylphenyl)ethane.
Workup
- distillationAcetone was distilled off
- additionn-hexane and cold water were added to the mixture
- washThe n-hexane layer was washed successively with a 1.6% aqueous solution of sodium hydroxide and water
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-53df0a967a7c4e67b74715491631a6e0
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04436939
Reaction notes
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