Ethyl Z- and E-2-vinyl-2-methylcyclobutanecarboxylate

Details Ethyl Z- and E-2-vinyl-2-methylcyclobutanecarboxylate Ethyl Z- and E-2-vinyl-2-methylcyclobutanecarboxylate

1974-10-25

1976-11-30

Weinberger, Lorraine A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260486H, 260488H, 260593H, 260617R, 260633, C07C 6974

Patent

active

039949532

ABSTRACT:
The present invention is concerned with a method for preparing grandisol, the major component of the boll weevil sex pheromone. This method involves the conversion of 4-chloro-2-butanone to 5-chloro-3-methyl-1-penten-3-ol, acid-catalyzed isomerization of the latter compound to E- and Z-5-chloro-3-methyl-2-penten-1-ol, followed by conversion to ethyl 3-[2-chloroethyl]-3-methyl-4-pentenoate by treatment with triethyl orthoacetate, cyclization of ethyl 3-[2-chloroethyl]-3-methyl-4-pentenoate to ethyl Z- and E-2-vinyl-2-methylcyclobutanecarboxylate by reaction with base, conversion of ethyl Z- and E-2-vinyl-2-methylcyclobutanecarboxylate to Z- and E-2-[2-methyl-2-vinylcyclobutyl]-2-propanol by reaction with methyllithium, and the conversion of the latter compound to grandisol by reaction with diborane and basic hydrogen peroxide followed by dehydration.

REFERENCES:
tumlinson et al., J. Org. Chem., 36, pp. 2616-2621 (1971).

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