Diethyl benzylphosphonate → 1-Chloro-4-(2-phenylethenyl)benzene

HRID 2198510Notes

Reaction equation

HRID 2198510 reaction equation
C(OP([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)OCC)C.C(OP([CH:24](O)[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)(=O)OCC)C>O1CCCC1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH:24]=[CH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14122Diethyl benzylphosphonateHCID 89363Diethyl P-((4-chlorophenyl)hydroxymethyl)phosphonate

Product 1

HCID 953041-Chloro-4-(2-phenylethenyl)benzeneYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

22.8 g (0.1 mol) of benzylphosphonic acid diethyl ester were added dropwise to a solution, cooled to 0° to 5° C., of 22.4 g (0.2 mol) of potassium tert.-butylate in 100 ml of tetrahydrofuran (dried over sodium) in the course of 15 minutes. The mixture was stirred for one hour; a solution of 28 g (0.1 mol) of α-hydroxy-4-chlorobenzylphosphonic acid diethyl ester in 50 ml of tetrahydrofuran was then added to the mixture, while cooling to 0° to 5° C., and the mixture was stirred at room temperature (about 20° C.) for a further 15 hours. It was then poured into 1 liter of ice-water, filtered off and dried. 18 g (84% of theory) of 1-(4-chlorophenyl)-2-phenyl-ethylene were thus obtained in the form of colorless crystals of melting point 130° C.

Workup

  1. temperaturewhile cooling to 0° to 5° C.
  2. stirringthe mixture was stirred at room temperature (about 20° C.) for a further 15 hours
  3. filtrationfiltered off
  4. customdried

Sources & evidence

ORD record
ord-07d8db9a8db54876927569c6553d5b38
Source dataset
uspto-grants-1982_11
Patent number
US04358409

Reaction notes

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