(+-)-alpha-Pinene → HCID 68865026, compound

Participants

Reaction Steps

A mixture of 20.0 g acryloyl chloride (0.22 mol) and 3.01 g zinc chloride (0.02 ml, 0.1 eq.) in 150 ml ethylene chloride was treated with a soln. of 350 ml α-pinene ((1S-(−)/(1R)-(+) 90:10, 2.20 mol, 10 eq.) in 250 ml ethylene chloride and the resulting mixture was stirred 1 h at 25° C. and 4 h at 50° C. After cooling, the reaction mixture was washed with aq. sat. NaCl soln. and aq. sat. NaHCO3 soln. The aq. phases were extracted with Et2O, dried (Na2SO4), and concentrated. The crude product (48 g) was filtered (SiO2, hexane/Et2O 200:6→200:10) and the residue (1.42 g) treated with 300 mg LiOH.H2O in 15 ml MeOH at 25° C. for 7 h. The resulting mixture was poured into aq. sat. NaCl soln., extracted with hexane and the org. phases dried with Na2SO4, FC (SiO2, hexane/Et2O 30:1) gave 347 mg (0.8%) of compound 10. Boiling point: 80° C. at 0.07 torr (0.09 mbar).

Provenance & Evidence