Tetrahydrofuran → 1-Trifluoromethoxy-4-(2-methoxyvinyl)benzene

THF (1.8 l) was added to methoxymethyltriphenylphosphine chloride (350 g, 1.02 mol), followed by adding to the mixture, potassium-t-butoxide (114 g, 1.02 mol), stirring the mixture at the same temperature, for 3 hours, dropwise adding to the reaction solution, a 750 ml THF solution of commercially available 4-trifluoromethoxybenzaldehyde (150.0 g, 0.79 mol), stirring the mixture at the same temperature for one hour, further stirring it at room temperature for 3 hours, adding water (1.5 l) to the reaction solution, extracting the resulting product with ethyl acetate, washing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water, drying over magnesium sulfate, distilling off the solvent, purifying the resulting yellow solution according to column chromatography treatment using heptane/ethyl acetate (3/2) as a developing solvent, on silica gel, and distilling the purified product under reduced pressure, by means of Vigoureux tube, to obtain 1-trifluoromethoxy-4-(2-methoxyvinyl)benzene (138 g, 0.63 mol). (b.p. 91° C. under 9 Torr). Yield: 79.7%.

1. additiondropwise adding to the reaction solution
2. stirringfurther stirring it at room temperature for 3 hours
3. extractionextracting the resulting product with ethyl acetate
4. washwashing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water
5. dry with materialdrying over magnesium sulfate
6. distillationdistilling off the solvent
7. custompurifying the resulting yellow solution
8. distillationon silica gel, and distilling the purified product under reduced pressure

ORD record

ord-c87c10b098ee4a67a210412b01fe2e57

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05702641