Oxalyl chloride → (10-Undecenyl)phosphono chloridic acid, ethyl ester

HRID 2214422Notes

Reaction equation

HRID 2214422 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

HCID 65578Oxalyl chlorideHCID 23420214Diethyl undec-10-en-1-ylphosphonate

Product 1

HCID 21054114(10-Undecenyl)phosphono chloridic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customSolvent was removed to dryness
  2. customthe excess oxalyl chloride was azeotropically removed with hexane three times (100 mL)
  3. customThe mixture was dried in a vacuum oven at 40° C. overnight
  4. customthe product was used without further purification

Sources & evidence

ORD record
ord-9d435b0541204cfdb080543ad308569e
Source dataset
uspto-grants-2006_09
Patent number
US07109184B2

Reaction notes

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