Process for preparing macrocyclic ketones

Details Process for preparing macrocyclic ketones Process for preparing macrocyclic ketones

1986-01-31

1987-10-13

Reamer, James H.

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

Organic compounds

Oxygen containing

568346, C07C 4565

Patent

active

047000074

ABSTRACT:
An improvement in a process for preparing a macrocyclic ketone having from 12 to 18 carbon atoms which comprises intramolecular cyclization of a lower alcohol diester of a straight chain alkanedicarboxylic acid having from 12 to 18 carbon atoms by acyloin condensation and reduction of the resulting 2-hydroxycycloalkanone is disclosed. The improvement comprises conducting the acyloin condensation in a water-immiscible organic solvent having a boiling point of not lower than 40.degree.C., subjecting the resulting organic solvent solution containing the 2-hydroxycycloalkanone to reduction, and conducting the reduction in the copresence of said organic solvent and water. The macrocyclic ketone can be prepared at high efficiency.

REFERENCES:
patent: 2529825 (1950-11-01), Stoll
patent: 2656390 (1953-10-01), Stoll
patent: 3228268 (1941-01-01), Hansley
patent: 3786099 (1974-01-01), Howell
Vao et al., Chem. Abst. vol. 94, #208417q (1981).
Oop et al., Org. Synthesis, 218 (1963).
Journal of the Chemical Society, No. 452, 1962, pp. 2348-2352, Dhekne et al.

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