Acetone → 2-(2,2-Dimethyl-2H-1,3-benzodioxol-5-YL)ethan-1-OL

1.7 g of 3,4-dihydroxyphenylacetic acid, a catalytic amount of p-toluenesulfonic acid, 10 ml of acetone and 10 ml of benzene were heated under reflux for 18 h. The reflux solution was dehydrated with Molecular Sieve 4A. The reaction mixture was concentrated and the obtained dark brown oil was dissolved in 20 ml of tetrahydrofuran. The solution was added to a suspension of 0.8 g of lithium aluminum hydride in 30 ml of tetrahydrofuran under cooling with ice. The mixture was stirred at room temperature for 1 h and then cooled with ice/water. 0.8 ml of water, then 0.8 ml of a 15% aqueous sodium hydroxide solution and finally 2.4 ml of water were added thereto and an insoluble substance was filtered off. The filtrate was concentrated and treated according to silica gel column chromatography (ethyl acetate/n-hexane=1:1) to obtain 1.1 g of the intended compound in the form of a colorless oil.

1. temperatureunder reflux for 18 h
2. concentrationThe reaction mixture was concentrated
3. dissolutionthe obtained dark brown oil was dissolved in 20 ml of tetrahydrofuran
4. additionThe solution was added to a suspension of 0.8 g of lithium aluminum hydride in 30 ml of tetrahydrofuran
5. temperatureunder cooling with ice
6. temperaturecooled with ice/water
7. addition0.8 ml of water, then 0.8 ml of a 15% aqueous sodium hydroxide solution and finally 2.4 ml of water were added
8. filtrationan insoluble substance was filtered off
9. concentrationThe filtrate was concentrated
10. additiontreated

ORD record

ord-fcce71eff21144199c7fe5ef95ebdcc2

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05292901