3-Chloro-2-methyl-1-propene → HCID 54366571, compound

Participants

Reaction Steps

In a manner similar to Example 6, 90 g of 6,6-dimethylbicyclo[3.1.1]hept-2-yl acetaldehyde (0.529 mole) in 40 ml of DMF, 108 g of potassium t-butoxide (0.91 mole) in 400 ml of DMF, and 93 g of methallyl chloride (1.02 moles) in 40 ml of DMF were reacted in the usual manner. After work-up the crude mixture of C- and O-alkylates, 112 g, was heated at 165°-175° C. for 4 hours. The crude product was dwastilled to afford 34.5 g of purified product (30% yield). BP 90° C./0.1 mmHg; 1H-NMR (300 MHz), δ 1.06 (3H, s), 1.16 s), 1.69 (3H, s), 1.3-2.6 (12H, m), 4.67 (1H, s), 4.74 (1H, s), 9.36 (1H, m); 13C-NMR (75 MHz), spectra consistent with assigned structures; IR (Neat) 2960, 2700, 1730, 1650, 1470, 1370, 890 cm-1 ; MS (m/e), 220 (M+), 205, 189, 177, 163, 149, 135, 121, 107, 93, 79, 69, 41 (Base);

Provenance & Evidence