2,2,2-Trifluoroacetophenone → HCID 12650829, compound

HRID 1382625Notes

Reaction equation

HRID 1382625 reaction equation
[Na].[F:2][C:3]([F:13])([F:12])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>[C:6]1([CH2:4][CH:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([F:13])([F:12])[F:2])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 99052,2,2-TrifluoroacetophenoneHCID 5360545Sodium

Product 1

HCID 12650829HCID 12650829, compoundYield 183.1%

Reagents, catalysts & solvents 2

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 702EthanolSolvent3×

Procedure

A solution of 456 g (1.17 moles) of benzyl-triphenylphosphoniumchloride (G. Wittig: Chem. Ber. 87, 1318 (1954)) in 1500 ml of dry ethanol is added to a solution of 27 g (1.17 g.-atoms) of sodium in 500 ml of dry ethanol at 0°-2° C. The resulting mixture is combined with a solution of 204 g (1.17 moles) of 2,2,2-trifluoroacetophenone in 100 ml of dry ethanol, and the mixture is allowed to stand overnight. The solution is evaporated, the residue is admixed with 800 ml of petroleum ether, filtered, and the filter cake is washed. The filtrate is evaporated, and the residue is distilled in vacuo. 268 g (92.5%) of 1,2-diphenyl-3,3,3-trifluoro-propane are obtained; b.p.: 107°-109° C./0.2 mm Hg, m.p.: 58°-61° C.

Workup

  1. customThe solution is evaporated
  2. filtrationfiltered
  3. washthe filter cake is washed
  4. customThe filtrate is evaporated
  5. distillationthe residue is distilled in vacuo

Sources & evidence

ORD record
ord-6884ac36c7bc4d62adf018668df83efe
Source dataset
uspto-grants-1989_02
Patent number
US04806685

Reaction notes

Loading…