Acetone → 5-Fluoro-2,2-dimethyl-2H-1,3-benzodioxole

HRID 2226096Notes

Reaction equation

HRID 2226096 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[CH3:10][C:11]([CH3:13])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)Cl>[CH3:10][C:11]1([CH3:13])[O:1][C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[O:9]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14812Phosphorus oxide (P4O10)HCID 1604584-Fluorocatechol

Product 1

HCID 189662825-Fluoro-2,2-dimethyl-2H-1,3-benzodioxoleYield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a flask were placed 40 g (0.31 mole) of 1,2-dihydroxy-4-fluorobenzene, 36.25 g (0.625 mole) of acetone, and 400 mL of methylene chloride. To this solution was added 133 g (0.937 mole) of phosphorus pentoxide in portions during a five minute period. This mixture was stirred at ambient temperature for approximately 16 hours after which the methylene chloride was decanted from the solid material in the flask. Ice was added to the flask, and the solid residue was dissolved in water and extracted with methylene chloride. The phases were separated, and the organic phase was combined with the methylene chloride solution that had been decanted from the reaction mixture. This solution was washed in succession with a 5% aqueous solution of sodium hydroxide and then with water. After being dried over anhydrous magnesium sulfate and filtered, the organic solution was evaporated under reduced pressure, leaving 29.3 g of 2,2-dimethyl-5-fluoro-1,3-benzodioxole as a residue. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customIn a flask were placed
  2. customwas decanted from the solid material in the flask
  3. additionIce was added to the flask
  4. dissolutionthe solid residue was dissolved in water
  5. extractionextracted with methylene chloride
  6. customThe phases were separated
  7. customhad been decanted from the reaction mixture
  8. washThis solution was washed in succession with a 5% aqueous solution of sodium hydroxide
  9. dry with materialAfter being dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customthe organic solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-16607fb47f1c4d9cba8fcdfc932b49f7
Source dataset
uspto-grants-1994_09
Patent number
US05346881

Reaction notes

Loading…