Mesitylene → HCID 21666955, compound

Participants

Reaction Conditions

Reaction Steps

Analogously to J. Am. Chem. Soc. 104, 3527-29 (1982), 3.42 g (10 mmol) of Co2 (CO)8 in 50 ml of mesitylene are placed in a 0.3 liter autoclave at 0°; 0.5 mol of 3,3,3-trifluoropropene are introduced, followed at room temperature in succession by 65 bars of carbon monoxide and 65 bars of hydrogen. The reaction mixture is heated to 110° C. and, by the addition of a (1:1) mixture (v/v) of CO and H2, the pressure is maintained constant at 130 bar. After absorption of the theoretical amount of the CO/H2 mixture (1-5 hours), the whole is cooled to 0° and the autoclave is returned to normal pressure. To the crude mixture, which has been rinsed out with a small amount of mesitylene, there is slowly added, at room temperature, a solution of 156.8 g (0.45 mol) of ethoxycarbonylmethylenetriphenylphosphorane in 600 ml of methylene chloride. After the mildly exothermic reaction has subsided, the whole is stirred at room temperature for 21/2 hours and then concentrated by evaporation. The residue is made into a slurry with pentane (approx. 100 ml), precipitated triphenylphosphine oxide is removed, and then distillation at reduced pressure is carried out. The desired ester is obtained in the form of a colourless oil (b.p. 78°-82°/26 mm Hg) in a yield of 50%.

Provenance & Evidence