Oxalyl chloride → (10-Undecenyl)phosphono chloridic acid, ethyl ester
Reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19])(=O)[O:5]CC)[CH3:2].C(Cl)(=O)C([Cl:23])=O>C(Cl)Cl>[CH2:9]([P:4]([Cl:23])(=[O:5])[O:3][CH2:1][CH3:2])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 10-undecenylphosphonic acid diethyl ester (53.51 g, 180 mmol) in CH2Cl2 (350 mL) was cooled to about −8° C. Oxalyl chloride (32 mL, 370 mmol, 2 eq.) was added slowly to the mixture, the mixture was warmed to room temperature and stirred overnight. Solvent was removed to dryness and the excess oxalyl chloride was azeotropically removed with hexane three times (100 mL). The mixture was dried in a vacuum oven at 40° C. overnight and the product was used without further purification. 1H NMR (400 MHz CDCl3) δ=5.8 (m, 1H), 5.0 (m, 2H), 4.3 (m, 2H), 2.2–2.0 (m, 4H), 1.7 (m, 2H), 1.5–1.2 (M, 15H). 31P NMR (CDCl3) δ=46.2.