Diethyl Ether → HCID 15039850, compound

Participants

Reaction Steps

2,2-dimethyl-nonan-3-ol, available as a concentrated solution in ether (ca. 0.23 moles, cf. previous procedure), was dissolved in ca. 350 mL CH2Cl2 in a 500 mL round bottom flask. With vigorous stirring and external cooling, pyridinium chlorochromate (PCC, 76.6 g, 0.355 mol) was added slowly. The reaction mixture turned black and began to warm. The reaction was stirred overnight at room temperature, and the supernatant was decanted from a black sludge which had formed. The sludge was extracted with ca. 40 mL of hexane, which was combined with the CH2Cl2 solution. This mixture was applied directly to a 100 g silica gel column, and eluted first with CH2Cl2/hexane and then with 10% ethyl acetate in hexane to yield 35.8 g crude, green-colored product. This material was rechromatographed; elution with hexane and careful evaporation at 25° C. on a rotary evaporator yielded 26.1 g 2,2-dimethyl-nonan-3-one (67% yield). 1H NMR (500 MHz, CDCl3), δ(ppm): 2.47 (t, 2H), 1.28 (br, 8H), 0.89 (t, 3H).

Provenance & Evidence