Hexafluoroacetone → HCID 19818990, compound

HRID 1195217Notes

Reaction equation

HRID 1195217 reaction equation
[CH2:1]=[CH:2][CH:3]1[O:5][CH2:4]1.[F:6][C:7]([F:15])([F:14])[C:8]([C:10]([F:13])([F:12])[F:11])=[O:9]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[F:6][C:7]([F:15])([F:14])[C:8]1([C:10]([F:13])([F:12])[F:11])[O:5][CH:3]([CH:2]=[CH2:1])[CH2:4][O:9]1

Participants

5

Reactant 2

HCID 12695HexafluoroacetoneHCID 13586Vinyloxirane

Product 1

HCID 19818990HCID 19818990, compoundYield 12.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Butadiene monoepoxide (9.8 g, 0.14 mole, Aldrich Chemical Co.) was mixed with hexafluoroacetone (50 g, 0.30 mole) in a 210 ml Hastelloy®C shaker tube in the presence of tetrabutylammonium bromide (0.12 g) and water (0.12 g). The tube was sealed and heated at 80° C. for 1 hour, 100° C. for 1 hour and 120° C. for 6 hours. The product mixture was distilled to afford the desired 2,2-bis(trifluoromethyl)-4-vinyl-1,3-dioxolane, 4.0 g (12.1% yield), as a clear, colorless liquid. Bp. 78°-80° C. 1H-NMR (CDCl3): δ 5.84 (m, 1H), 5.48 (m, 2H), 4.88 (dd, J=6.6, 5.4 Hz, 1H), 4.46 (t, J=6.6 Hz, 1H), 3.87 (t, J=6.6 Hz, 1H).

Workup

  1. customThe tube was sealed
  2. distillationThe product mixture was distilled

Sources & evidence

ORD record
ord-3a9be5d70fc14f608daed65660d8d582
Source dataset
uspto-grants-1992_05
Patent number
US05110938

Reaction notes

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