Dimethyl Sulfate → HCID 14793999, compound

Participants

Reaction Steps

To a stirred suspension of sodium hydride (46.8 g of a 60% oil dispersion, 1.15 mol) in tetrahydrofuran (240 mL) was added 2-methylhex-5-en-2-ol (120 g, 1.05 mol) in tetrahydrofuran (240 mL). Dimethylsulfate (75 mL, 0.79 mol) in tetrahydrofuran (120 mL) was added to the cooled (0~C.) mixture. The mixture was heated at reflux for 6 hours. Workup yielded 2-methoxy-2-methylhex-5-ene, bp40 53-58~C. (51.36 g); NMR(CDCl3)δ 1.1(s,6H), 1.5-1.6(m,2H), 2.0-2.2(m,2H), 3.2(s,3H), 4.8-5.1(m,2H), 5.7-6.0(m,1H); IR(neat) 2960, 2925, 1640, 1460, 1360, 1300, 1085 cm-1 ; MS(m/e) 43, 55, 73, 81, 95, 97, 113, 114.

Provenance & Evidence