Hydrochloric Acid → 2,6-Dichlorobenzylphosphonic acid

HRID 1154976Notes

Reaction equation

HRID 1154976 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[CH2:4][P:5](=[O:12])([O:9]CC)[O:6]CC.Cl>>[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[CH2:4][P:5](=[O:6])([OH:9])[OH:12]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 2795329Phosphonic acid, [(2,6-dichlorophenyl)methyl]-, diethyl ester

Product 1

HCID 18154112,6-Dichlorobenzylphosphonic acid

Procedure

O,O-Diethyl 2,6-dichlorobenzylphosphonate (1794 grams) and concentrated hydrochloric acid (2 l) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux for a period of 16 hours. The mixture was then cooled in the formation of a solid product. This product was recovered by filtration was washed with water and dried to yield the desired product 2,6-dichlorobenzylphosphonic acid having a melt point of 211° to 218° C.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for a period of 16 hours
  5. temperatureThe mixture was then cooled in the formation of a solid product
  6. filtrationThis product was recovered by filtration
  7. washwas washed with water
  8. customdried

Sources & evidence

ORD record
ord-0f6d94fb4ba848b382a683c5a8581fb0
Source dataset
uspto-grants-1981_11
Patent number
US04299615

Reaction notes

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