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Diethyl (Alpha, Beta, Beta, Beta -Tetrafluoropropionyl) -Malonate

IP.com Disclosure Number: IPCOM000097384D
Original Publication Date: 1962-Nov-01
Included in the Prior Art Database: 2005-Mar-07
Document File: 2 page(s) / 15K

Publishing Venue

IBM

Related People

Schumaker, R: AUTHOR [+2]

Abstract

Diethyl (Alpha, Beta, Beta, Beta -tetrafluoropropionyl)-malonate is prepared from Alpha, Beta, Beta, Beta -tetrafluoropropionyl chloride. See page 7, this issue. This malonate has the formula (Image Omitted) It is useful, inter alia, for the preparation of 3, 4, 4, 4-tetrafluorobutan- 2-one. See page 9, this issue. Preparation of the above malonate is as follows:

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Diethyl (Alpha, Beta, Beta, Beta -Tetrafluoropropionyl) -Malonate

Diethyl (Alpha, Beta, Beta, Beta -tetrafluoropropionyl)-malonate is prepared from Alpha, Beta, Beta, Beta -tetrafluoropropionyl chloride. See page 7, this issue. This malonate has the formula

(Image Omitted)

It is useful, inter alia, for the preparation of 3, 4, 4, 4-tetrafluorobutan- 2-one. See page 9, this issue. Preparation of the above malonate is as follows:

A solution is prepared from 160 g (1. 0 mole) diethyl malonate, 250 ml dry benzene, and 40 g (0. 87 mole) absolute ethanol. A Approximately 10 ml of this solution is added to a mixture of 24 g (1. 0 mole) magnesium turnings, 50 ml dry benzene, 8 g (0. 18 mole) absolute ethanol, and 0. 5 ml carbon tetrachloride. This mixture is heated to reflux, whereupon a vigorous reaction starts. The heat is turned off and the diethyl malonate solution is added at such a rate as to keep the reaction mixture boiling. The addition is completed in two and one-half hours. Refluxing was continued for an additional hour at which time the magnesium was completely consumed. Approximately 75 ml solvent was distilled off to remove any excess ethanol. The solution is cooled to 15 degrees C and a solution of 97g (0.59 mole) Alpha, Beta, Beta, Beta -tetrafluoropropionyl chloride in 100 ml dry benzene is added slowly to the cooled reaction mixture with vigorous stirring. The addition required 40 minutes. The thick, yellow mixture was heated to reflux for one hour and...