ChemicalBook CAS DataBase List Bis(hexafluoroisopropyl) carbonate

Bis(hexafluoroisopropyl) carbonate synthesis

4synthesis methods

Product Name:Bis(hexafluoroisopropyl) carbonate
CAS Number:18925-66-1
Molecular formula:C7H2F12O3
Molecular Weight:362.07

32315-10-9 Synthesis

32315-10-9
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$10.00/1g

920-66-1 Synthesis

920-66-1
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$6.00/10g

18925-66-1
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Yield:18925-66-1 78%

Reaction Conditions:

Stage #1: 1,1,1,3',3',3'-hexafluoro-propanolwith sodium hydride in diethyl ether at 0 - 20; for 0.833333 h;
Stage #2: bis(trichloromethyl) carbonate in diethyl ether at 0 - 20; for 2 h;

Steps:

1 Example 1

A 500 mL flask was charged with sodium hydride (60% dispersion, 8.16 g, 204 mmol). Ether (100 mL) was added and the reaction was cooled to 0 °C. A solution of 1,1, 1,3,3,3- hexafluoro-2-propanol (1) (21 mL, 204 mmol) in ether (40 mL) was added via addition funnel over 10 min. The reaction became clear by the end of the addition. The reaction was stirred at 0 °C for 20 min and then allowed to warm to room temperature and stirred for 20 min. The solution was transferred via cannula (-10 mL/min) to a 0 °C solution of triphosgene (10 g, 33.7 mmol) in ether (40 mL) resulting in an exothermic reaction and formation of a precipitate. The solution was stirred at room temperature for 2 h. The reaction was filtered and the solids were washed with ether (50 mL). The filtrate was carefully concentrated (water bath maintained at 36 °C, and vacuum at 500 Torr) via rotary evaporation to yield a cloudy solution, which partitions into a top (organic) and bottom (fluorous) layer. The bottom layer was retained to give bis[2,2,2-trifluoro-l- (trifluoromethyl)ethyl] carbonate (2) (8.00 g, 78% by weight solution in ether, 51% yield) as a solution. This was used in the next reaction without further purification. 1H NMR (400 MHz, Chloroform-^ δ 5.50 (hept, J = 5.7 Hz, 1H). ¹³C MR (101 MHz, CDC1₃) δ 151.56, 123.85, 121.02, 118.24, 115.41, 72.51, 72.16, 71.80, 71.45, 71.09.

References:

WO2017/143283,2017,A1 Location in patent:Paragraph 00133

67-66-3 Synthesis