Nitric Acid → HCID 21395802, compound

HRID 1973269Notes

Reaction equation

HRID 1973269 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].C(OC(=O)C)(=O)C.[Cl:12][C:13]([F:26])([F:25])[C:14]1([C:21]([Cl:24])([F:23])[F:22])[O:18][CH:17]([CH2:19]O)[CH2:16][O:15]1>O>[N+:1]([O-:4])([O:3][CH2:19][CH:17]1[CH2:16][O:15][C:14]([C:13]([Cl:12])([F:25])[F:26])([C:21]([Cl:24])([F:22])[F:23])[O:18]1)=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 21395814HCID 21395814, compound

Product 1

HCID 21395802HCID 21395802, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

34 ml nitric acid (96%) is added slowly to 43 ml chilled acetic anhydride. Then, 14.8 grams of 2,2-bis(chlorodifluoromethyl)-4-hydroxymethyl-1,3-dioxolane, is added dropwise with magnetic stirring over a 30 minute period to the chilled mixed acid (0° to -10° C.). An additional 25 minutes of stirring is allowed. The reaction mixture is drowned in 250 ml of cold tap water forming a small lower liquid layer. Ether extraction (3 × 75 ml) removed the lower layer and all of the yellow coloration. The ether solution is washed several times with water and then dried over Na2SO4, filtered and evaporated on a rotary evaporator. The cloudy residue is redissolved in ether, treated with Na2SO4, decanted and evaporated as before. The bright yellow liquid is redissolved in ether and treated with activated carbon (DARCO G-60), then filtered (colorless), and reevaporated to yield the above named product.

Workup

  1. additionmixed acid (0° to -10° C.)
  2. stirringAn additional 25 minutes of stirring
  3. extractionEther extraction (3 × 75 ml)
  4. customremoved the lower layer
  5. washThe ether solution is washed several times with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated on a rotary evaporator
  9. dissolutionThe cloudy residue is redissolved in ether
  10. additiontreated with Na2SO4
  11. customdecanted
  12. customevaporated as before
  13. dissolutionThe bright yellow liquid is redissolved in ether
  14. additiontreated with activated carbon (DARCO G-60)
  15. filtrationfiltered (colorless)
  16. customreevaporated
  17. customto yield the above named product

Sources & evidence

ORD record
ord-c030db9d61f3403595ed4b6a3fd3a0cd
Source dataset
uspto-grants-1976_12
Patent number
US03996376

Reaction notes

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