3-Chloro-2-methyl-1-propene → HCID 22914091, compound

Participants

Reaction Steps

In a similar manner to Example 6, 100 g of the aldehyde from Example 58 at a purity of 85% (0.47 mole) in 75 ml of DMF, 82 g of potassium t-butoxide (0.69 mole) in 500 ml of DMF, and 78 g of methallyl chloride (0.86 mole) in 50 ml of DMF were reacted in the usual way. In this way 116.2 g of crude O- and C-alkylates (58.1:33.8) were obtained. The crude product was heated at 165°-170° C. for 2 hours. The crude aldehyde was distilled to afford 94.1 g of purified product (85% yield). BP 85° C./0.05 mmHg; 1H-NMR (300 MHz), δ 0.95 (3H, s), 0.96 (3H, s), 1.18 (3H, s), 1.2-1.4 (2H, m), 1.59 (3H, s), 1.7-2.5 (9H, m), 4.64 (1H, s), 4.80 (1H, s), 9.57 (1H, s); 13C-NMR (75 MHz), spectra consistent with assigned structures; IR (Neat), 2960, 2700, 1725, 1645, 1470, 1370, 895 cm-1 ; MS (m/e), 234 (M+), 219, 203, 191, 177, 163, 151, 135, 123, 109, 97, 81, 41 (Base);

Provenance & Evidence