Formaldehyde → HCID 12832600, compound

HRID 1105723Notes

Reaction equation

HRID 1105723 reaction equation
[Na].[P:2]([O-:9])([O:6][CH2:7][CH3:8])[O:3][CH2:4][CH3:5].[CH2:10]=[O:11].[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:14]=1[C:15](Cl)=[O:16]>C(OCC)C>[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:14]=1[C:15]([O:11][CH2:10][P:2](=[O:9])([O:6][CH2:7][CH3:8])[O:3][CH2:4][CH3:5])=[O:16]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 783922,6-Dichlorobenzoyl chlorideHCID 3780918DiethylphosphiteHCID 5360545Sodium

Product 1

HCID 12832600HCID 12832600, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 5.8 grams (0.25 mole) of sodium metal in 150 ml of diethyl ether, under an argon atmosphere and at 15°-20°, was added dropwise 34.5 grams (0.25 mole) of diethyl phosphite. Complete addition required 60 minutes. Upon completion of the addition, the reaction mixture was kept at 15°-20° for 1 hour, then heated under reflux for 1 hour. The reaction mixture was cooled to 15° and 9.0 grams (0.30 mole) of paraformaldehyde was added in portions during a 10-15 minute period. Upon completion of the addition the reaction mixture was stirred at ambient temperature for 18 hours. After this period 52.4 grams (0.25 mole) of 2,6-dichlorobenzoyl chloride in 50 ml of diethyl ether was added dropwise during a 37-minute period. Upon completion of the addition the reaction mixture was stirred for 1.5 hours, then filtered. The filtrate was evaporated under reduced pressure to a residual oil. Impurities were removed from the residual oil by high vacuum distillation. The pot residue was subjected to column chromatography on 600 grams of silica gel using ethyl acetate as eluent. The appropriate fractions were combined and distilled under high vacuum to give 13.6 grams of diethyl (2,6-dichlorobenzoyloxy)methylphosphonate; bp 164°-167°/0.01 mm. The nmr and the ir spectra were consistent with the proposed structure.

Workup

  1. additionaddition required 60 minutes
  2. additionUpon completion of the addition
  3. temperatureheated
  4. temperatureunder reflux for 1 hour
  5. temperatureThe reaction mixture was cooled to 15°
  6. additionUpon completion of the addition the reaction mixture
  7. additionUpon completion of the addition the reaction mixture
  8. stirringwas stirred for 1.5 hours
  9. filtrationfiltered
  10. customThe filtrate was evaporated under reduced pressure to a residual oil
  11. customImpurities were removed from the residual oil by high vacuum distillation
  12. distillationdistilled under high vacuum

Sources & evidence

ORD record
ord-12e4d6bc805245afb1a3913b7a3c5ead
Source dataset
uspto-grants-1982_01
Patent number
US04309566

Reaction notes

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