Cyclohexene oxide → HCID 12043059, compound

Temperature

-78 °C

Cyclohexene oxide (90.2 ml; 0.89 mol) was added dropwise to a mechanically stirred mixture of trimethoxybenzene (I, 100 g; 0.594 mol) and aluminum chloride (118.82 g; 0.89 mol) in dichloromethane (500 ml) cooled at -78° C. The addition was done over a period of 50 min. The reaction mixture was allowed to stir at that temperature and the progress of the reaction monitored by TLC (tlc system 25% ethyl acetate-pet ether; anisaldehyde spray; pdt. Rf-value 0.35). The reaction mixture was worked up after 3 hours by adding cold-water (400 ml) and extracting with ethyl acetate (4×400 ml). The combined organic layers were washed with water, brine, and dried over sodium sulphate. The solvents were removed in-vacuo at a rotary evaporator. The oily residue was crystallized from pet ether (400 ml) to get the crystals of the title compound (62 g). The mother liquor, on evaporation of the solvents followed by chromatography over silica gel (column diam. 9.5 cm; silica gel 800 g; eluent 10, 25 and 40% ethyl acetate-pet ether), gave 28 g of the title compound. In total, 90 g (yield 57%; mp. 125-27° C.) of the title compound was isolated.

1. additionThe addition
2. waitThe reaction mixture was worked up after 3 hours
3. extractionextracting with ethyl acetate (4×400 ml)
4. washThe combined organic layers were washed with water, brine
5. dry with materialdried over sodium sulphate
6. customThe solvents were removed in-vacuo
7. customat a rotary evaporator
8. customThe oily residue was crystallized from pet ether (400 ml)

ORD record

ord-02fc833c56e64df1b62e0c7162adeceb

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06159988