Accession Number:

AD0450822

Title:

CYCLOHEXANE COMPOUNDS. III. THE 1-METHOXY AND 1-ETHOXY-2-HYDROXY-3-BROMOCYCLOHEXANES,

Descriptive Note:

Corporate Author:

DEFENCE CHEMICAL BIOLOGICAL AND RADIATION LABS OTTAWA (ONTARIO)

Personal Author(s):

• Bannard, R. A. B.
• Hawkins, L. R.

Report Date:

1961-02-23

Pagination or Media Count:

14.0

Abstract:

1ALPHA-Methoxy-2beta-hydroxy-3alpha-bromocyclohexane and 1alpha-methoxy-2alpha-hydroxy-3betabromocyclohexane have been prepared by the action of hydrobromic acid on 1beta-methoxy-2alpha, 3alpha-epoxycyclohexane and 1alpha-methoxy2alpha,3alpha-epoxycyclohexane respectively. Assignment of stereochemical configuration to 1alpha-methoxy-2beta-hydroxy-3alpha-bromocyclohexane was made by catalytic debromination of the phenyl- and 1-naphthyl-urethane to derivatives of 2beta-methoxy-1alpha-cyclohexanol. An alternative proof of sturcture was obtained by de-etherification of the bromohydrin to 3alpha-bromo-1alpha,2beta-cyclohexanediol, which was catalytically debrominated to 1alpha, 2beta-cyclohexanediol and oxidized via periodate to 2-bromoadipaldehyde, isolated as the bis-2,4-dinitrophenylhydrazone. The structure of 1alpha-methoxy-2alpha-hydroxy-3beta-bromocyclohexane was established by de-etherification to 3beta-bromo-1alpha,2alpha-cyclohenanediol, which was oxidized by periodate 10 times more rapidly than its isomer. The corresponding ethoxy compounds were prepared and their structures were elucidated in a completely analogous manner. Author

Descriptors:

• *CYCLOHEXANES
• *CYCLOHEXANOLS
• SYNTHESIS(CHEMISTRY)
• SYNTHESIS(CHEMISTRY)
• ORGANIC OXYGEN COMPOUNDS
• BROMINE COMPOUNDS
• HYDROXIDES
• CHEMICAL PROPERTIES
• CHEMICAL REACTIONS

Subject Categories:

Distribution Statement:

APPROVED FOR PUBLIC RELEASE