Benzyl Alcohol → Benzene, [[[2-(chloromethyl)-2-propenyl]oxy]methyl]-

Benzyl alcohol (3.5 mL, 33.6 mmol) and DMF (8 mL) were added to a suspension of NaH (60% suspension in mineral oil, 1.8 g, 43.7 mmol, washed with hexane before use) in THF (35 mL). The resulting mixture was stirred for 30 minutes at room temperature and then 1 h at reflux. The mixture was cooled to room temperature and slowly added over 1 h to a solution of 3-chloro-2-chloromethyl-propene (4.2 g, 33.6 mmol) in THF (40 mL). The reaction was stirred at room temperature for 18 h, quenched with brine/water (1:1) and extracted with Et2O. The organic phase was dried (MgSO4), filtered and concentrated. Chromatography (SiO2, EtOAc:Petrol 1:9) to give the title compound (3.1 g) as a colourless oil. 1H NMR (CDCl3): 7.46-7.29 (5H, m), 5.35 (1H, s), 5.30 (1H, d), 4.56 (2H, s), 4.24-4.06 (4H, m).

1. temperature1 h at reflux
2. temperatureThe mixture was cooled to room temperature
3. stirringThe reaction was stirred at room temperature for 18 h
4. customquenched with brine/water (1:1)
5. extractionextracted with Et2O
6. dry with materialThe organic phase was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-8a28fcd5cc064ee0875c64af9eb43fc9

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018214B2