ChemicalBook CAS DataBase List 3-Penten-2-one, 1,1,1-trifluoro-4-methyl-

3-Penten-2-one, 1,1,1-trifluoro-4-methyl- synthesis

4synthesis methods

Product Name:3-Penten-2-one, 1,1,1-trifluoro-4-methyl-
CAS Number:400-31-7
Molecular formula:C6H7F3O
Molecular Weight:152.11

360-95-2 Synthesis

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3-Penten-2-one, 1,1,1-trifluoro-4-methyl-

400-31-7
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Yield:400-31-7 68%

Reaction Conditions:

Stage #1: 2,2,2-Trifluoro-1-morpholin-4-yl-ethanone;2-methylpropen-1-ylmagnesium bromide in tetrahydrofuran at 0 - 22; for 1.33 h;
Stage #2: with hydrogenchloride in tetrahydrofuran;water at 0 - 30;

Steps:

1

2-Methyl-l-propenylmagnesium bromide (0.5M in THF, 2.4 L, 1.2 mol) was cooled to 0⁰C. N-trifluoroacetylmorpholine (198.1 g, 1.082 mol) was added dropwise over 20 minutes to the Grignard solution at a rate such that the temperature did not exceed 10⁰C. The reaction mixture was allowed to stir at 15°C-22°C for 1 hour. The reaction mixture was cooled to 0⁰C and treated dropwise with 300 mL of concentrated hydrochloric acid, keeping the temperature below 30⁰C. The reaction was further diluted with 900 mL of water and 700 mL of dodecane, and the layers were cut. The organic phase was washed four times with a solution of 1.1 L of water and 300 mL of methanol, then with 1.2 L of water, and finally dried over 100 g of 4 A molecular sieves for 16 hours. The solution was filtered away from the molecular sieves and distilled at 150 mmHg (bath temperature up to 110⁰C) to give l,l,l-trifluoro-4-methyl-3-penten-2-one (699.3 g, 16 wt.%, thus 111.9 g 1 , 1 , 1 -trifluoro-4- methyl-3-penten-2-one, 68% yield) as a solution in THF.

References:

WO2010/141331,2010,A2 Location in patent:Page/Page column 14-15

38614-36-7
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104863-67-4 Synthesis