Reacción #574096

Ecuación de reacción

3,4-dihydroxyphenylacetic acid

vinyl acetate

sodium hydroxide

lithium aluminum hydride

→

intended compound

Rendimiento 74.6%

5-(2-Hydroxyethyl)-2-methyl-1,3-benzodioxole

Rendimiento 74.6%

Disolventes

toluene

ethyl acetate

tetrahydrofuran

water

water

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water
2. 2
   SecadoThe organic layer was dried over magnesium sulfate
3. 3
   workup.DISTILLATIONthe solvent was distilled off
4. 4
   OtroAn oil thus obtained
5. 5
   Temperaturaunder cooling with ice
6. 6
   workup.STIRRINGThe mixture was stirred at room temperature for 1 h
7. 7
   Filtraciónan insoluble matter was filtered off
8. 8
   ConcentraciónThe filtrate was concentrated
9. 9
   workup.ADDITIONtreated

Procedimiento

A suspension of 1.0 g of 3,4-dihydroxyphenylacetic acid, 1.4 g of vinyl acetate, 6 mg of mercury oxide (yellow) and 0.03 ml of boron fluoride/ethyl etherate in 9 ml of toluene was stirred at room temperature for 14 h. The reaction mixture was diluted with ethyl acetate and washed with water and an aqueous common salt solution. The organic layer was dried over magnesium sulfate and the solvent was distilled off. An oil thus obtained was dissolved in 10 ml of tetrahydrofuran and the solution was added dropwise to a suspension of 0.5 g of lithium aluminum hydride in tetrahydrofuran under cooling with ice. The mixture was stirred at room temperature for 1 h. 0.5 ml of water, then 0.5 ml of a 15% aqueous sodium hydroxide solution and finally 1.5 ml of water were added thereto and an insoluble matter was filtered off. The filtrate was concentrated and treated according to silica gel column chromatography (ethyl acetate/hexane=1:1) to obtain 0.8 g of the intended compound in the form of a colorless oil.

Fuente