Triethyl phosphite → Diethyl 4-phenylbutylphosphonate

HRID 256324Notes

Reaction equation

HRID 256324 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:12]([O:14][P:15]([O:19]CC)[O:16][CH2:17][CH3:18])[CH3:13]>>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:15](=[O:19])([O:16][CH2:17][CH3:18])[O:14][CH2:12][CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 78543(4-Chlorobutyl)benzene

Product 1

HCID 13102400Diethyl 4-phenylbutylphosphonateYield 84.1%

Conditions

Temperature
185 °C

Procedure

A mixture of 4-phenylbutyl chloride (8.0 g, 47.5 mmole) and triethylphosphite (15.0 ml, 72 mmole) was heated at reflux (bath temperature 185° C.) under argon for 41.5 hours. Distillation of the mixture gave pure diethyl (4-phenylbutyl)phosphonate (10.8 g, 84%) as a colorless liquid, b.p. 152°-154° C. (1.0 mmHg). TLC (EtOAc) single spot Rf =0.55.

Workup

  1. temperaturewas heated
  2. distillationDistillation of the mixture

Sources & evidence

ORD record
ord-b56b5521a0d0472694e4d02edfc34ec4
Source dataset
uspto-grants-1987_10
Patent number
US04703043

Reaction notes

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