Chloroethane → Diethyl benzoylphosphonate

HRID 329222Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:10]([O:17]CC)([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13].C(Cl)C>>[C:1]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6337Chloroethane

HCID 7412Benzoyl chloride

HCID 31215Triethyl phosphite

Product 1

HCID 220226Diethyl benzoylphosphonateYield 97.4%

Procedure

To 140.57 grams (1.0 mole) of benzoyl chloride at 90° C there were added 166.2 grams (1.0 mole) of triethyl phosphite over a period of 1 hour. Ethyl chloride evolution ceased at the end of this period. The unreacted benzoyl chloride and triethyl phosphite were removed by distillation at reduced pressure, terminal conditions being 100° C and 8 mm, leaving a residue of 236 grams (90% yield) of diethyl benzoylphosphonate which was reacted with diethyl sodium phosphite as in Example 1 to produce tetraethyl phenyl hydroxymethane diphosphonate. This was hydrolyzed and the hydrolysis product purified in the same manner as in Example 1 to produce phenyl hydroxymethane diphosphonic acid as a viscous syrup having an acid number of 822 mg KOH/mg (Theroy is 835 mg KOH/gm); % P 22.8 (Theory 22.9%).

Workup

customThe unreacted benzoyl chloride and triethyl phosphite were removed by distillation at reduced pressure, terminal conditions
custombeing 100° C

Sources & evidence

ORD record: ord-4b143721646d4431b493c2337d58561b
Source dataset: uspto-grants-1977_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04020091

Reaction notes

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