Scale-up and synthesis of 1-methoxycyglohepta-1,3,5-triene

Details Scale-up and synthesis of 1-methoxycyglohepta-1,3,5-triene Scale-up and synthesis of 1-methoxycyglohepta-1,3,5-triene

1989-11-27

1990-12-18

Lone, Werren B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568669, C07C 4100, C07C 4318

Patent

active

049788060

ABSTRACT:
A method for preparation of 1-methoxycyclohepta-1,3,5-triene in commercial quantities, which comprises the steps of heating 7,7-dichloro-1-methoxybicyclo[4.1.0]heptane in a refluxing reaction solvent comprising a lower boiling aromatic amine, at reflux, until suitable amounts of 1-methoxycyclohepta-1,3,5-triene have been produced, and recovering the 1-methoxycyclohepta-1,3,5-triene. Suitable reaction solvents include 2-picoline, pyridine and 2,6-lutidine. The method according to the present invention results in safer temperature control in the production of 1-methoxycyclohepta-1,3,5-triene, and increased yields.

REFERENCES:
patent: 4249025 (1981-06-01), Hydro
patent: 4506102 (1985-03-01), Kaufhold et al.
Gogery et al., "Canadian Jour. Chem.", 29:938-945 (1951).
Garbisch, "J. Org. Chem.", vol. 30, p. 2109 (1965).
Parham et al., "J. Amer. Chem. Soc.", vol. 84, p. 1755 (1962).
Lindsey et al., "Tetrahedron", vol. 21, p. 1673 (1965).

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