Dichloromethane → 1-Methyladamantane

A solution of 15 g (0.1 mole) of tricyclo[5.3.1.03,8 ]-undecane (II) in 100 ml of methylene chloride was agitated at 0°C, and 2.0 g (0.015 mole) of anhydrous aluminum chloride was added to the solution. The mixture was heated and refluxed under agitation for 6 hours, and the resulting reaction mixture was allowed to cool and poured over 100 ml of ice water. The organic layer was separated, and the water layer was extracted with methylene chloride. The methylene chloride extract was combined with the organic layer, and the mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and then with water, and then dried over anhydrous sodium sulfate. Methylene chloride was distilled off and the residue was sublimed to obtain 13.7 g (yield: 91 wt.%) of 1-methyladamantane. All of the IR, NMR and MS spectra were in agreement with those of the authentic sample synthesized from tetramethylenenorbornane according to the method of Schleyer, et al. [Tetrahedron Letters, 305 (1961)].

1. temperatureThe mixture was heated
2. temperaturerefluxed under agitation for 6 hours
3. customthe resulting reaction mixture
4. temperatureto cool
5. customThe organic layer was separated
6. extractionthe water layer was extracted with methylene chloride
7. extractionThe methylene chloride extract
8. washthe mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate
9. dry with materialwith water, and then dried over anhydrous sodium sulfate
10. distillationMethylene chloride was distilled off

ORD record

ord-641cf8e644d04138817b86d2d286656a

Source dataset

uspto-grants-1976_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03976706