3-Chloro-2-methyl-1-propene → HCID 22914112, compound

Participants

Reaction Conditions

Reaction Steps

Similar to Example 6, 17.0 g of 3-(1,1-dimethylethyl)cyclohexane carboxaldehyde (prepared by the method of E. Heilweil and J. Virgilio, Organic Preparations and Procedures, 14 (1-2), 9 (1982) at a purity of 87% (0.088 mole) in 20 ml of DMF, 11.9 g of potassium t-butoxide (0.10 mole) in 60 ml of DMF, and 12.0 g of methallyl chloride (0.13 mole) in 10 ml of DMF were reacted in the usual manner. The resulting mixture of O- and C-alkylates, 21.6 g, was heated at 155° C. for 1 hour. The crude aldehyde so obtained, 19 g, was distilled to afford 8.7 g of purified product (45% yield). BP 57° C./0.1 mmHg; 1H-NMR (300 MHz), δ 0.85 (9H, s), 0.97-1.45 (3H, m), 1.66 (3H, s), 1.68-1.74 (3H, m), 2.03-2.40 (5H, m), 4.66 (1H, s), 4.84 (1H, s), 9.50 (1H, s); 13C-NMR (75 MHz), δ 23.26, 24.63, 26.60, 27.34, 31.40, 32.46, 33.79, 44.31, 47.74, 50.56, 115.33, 140.77, 207.33; IR (Neat), 2970, 2690, 1720, 1635, 1450, 1360, 895 cm-1 ; MS (m/e), 222 (M+), 207, 166 (Base), 137, 123, 109, 95, 81, 57, 41.

Provenance & Evidence