Hydrochloric Acid → HCID 13902891, compound

HRID 1646090Notes

Reaction equation

HRID 1646090 reaction equation
[CH:1]([P:4]1(=[O:12])[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[CH2:6][O:5]1)=[C:2]=[CH2:3].CC1(C)COP(C#CC)(=O)[O:16]C1.O.NN.Cl>>[CH2:1]([P:4]1(=[O:12])[O:5][CH2:6][C:7]([CH3:10])([CH3:11])[CH2:8][O:9]1)[C:2]([CH3:3])=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 114128111,3,2-Dioxaphosphorinane, 5,5-dimethyl-2-(1,2-propadienyl)-, 2-oxideHCID 11994960HCID 11994960, compound

Product 1

HCID 13902891HCID 13902891, compoundYield 57.5%

Procedure

A solution mixture of II and III obtained in Reference Example 1 was stirred under cooling with ice and 510 g (10.2 mol) of hydrazine monohydrate was dropwise added thereto. After the completion of dropwise addition, the solution mixture was stirred for 30 minutes (the reaction was completed in ten minutes), and 11.2 kg of 10% by weight hydrochloric acid was added thereto. The solution mixture was stirred for one hour at room temperature and 5.0 kg of the solvent was distilled off. The solution was subjected to salting-out by addition of 1.38 kg of sodium chloride and extracted 2 times with 15.8 kg of chloroform. The chloroform layers were combined and dried over anhydrous sodium sulfate, followed by filtration. The solvent was distilled off, and the residue was dissolved in 3.5 kg of toluene and cooled with ice. The crystal thus precipitated was collected by filtration by means of suction and washed with 1.0 kg of toluene cooled and dried to obtain 1,000 g (yield: 57.5% through 4 steps) of the desired product of 2-acetonyl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane as colorless crystal.

Workup

  1. customobtained in Reference Example 1
  2. additionwas dropwise added
  3. additionAfter the completion of dropwise addition
  4. stirringthe solution mixture was stirred for 30 minutes (the reaction
  5. waitwas completed in ten minutes
  6. stirringThe solution mixture was stirred for one hour at room temperature
  7. distillation5.0 kg of the solvent was distilled off
  8. additionThe solution was subjected to salting-out by addition of 1.38 kg of sodium chloride
  9. extractionextracted 2 times with 15.8 kg of chloroform
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfollowed by filtration
  12. distillationThe solvent was distilled off
  13. dissolutionthe residue was dissolved in 3.5 kg of toluene
  14. temperaturecooled with ice
  15. customThe crystal thus precipitated
  16. filtrationwas collected by filtration by means of suction
  17. washwashed with 1.0 kg of toluene
  18. temperaturecooled
  19. customdried

Sources & evidence

ORD record
ord-9a60388677d44bf58b6287ac85e80f40
Source dataset
uspto-grants-1993_01
Patent number
US05177237

Reaction notes

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