Phenol → Methyl 3-(phenyl-methoxyphosphinyl)-2-chloropropionate

Reaction equation

[C:1]1([P:7](=[O:12])([O:10][CH3:11])OC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][C:14](=[CH2:19])[C:15]([O:17][CH3:18])=[O:16].C1(O)C=CC=CC=1>>[C:1]1([P:7]([O:10][CH3:11])([CH2:19][CH:14]([Cl:13])[C:15]([O:17][CH3:18])=[O:16])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 996Phenol

HCID 6659Methyl 2-chloroacrylate

HCID 75234Phosphonic acid, phenyl-, dimethyl ester

Product 1

HCID 15052091Methyl 3-(phenyl-methoxyphosphinyl)-2-chloropropionateYield 90.1%

Procedure

138 g of dimethyl phenylphosphonate are slowly added at 20° C. under nitrogen to a solution of 120.5 g of methyl 2-chloroacrylate and 94 g of phenol. After a reaction time of 3 hours at 70° C. phenetole is removed by vacuum distillation. The residue represents 267 g of crude product with a 93.0% purity, which corresponds to a theoretical yield of 90.1%.