AMMONOLYSIS OF 1,2-EPOXYCYCLOHEXANE AND TRANS-2-BROMOCYCLOHEXANOL

Authors
  1. Hawkins, L.R.
  2. Bannard, R.A.B.
Corporate Authors
Defence Research Chemical Labs, Ottawa ONT (CAN)
Abstract
Optimum conditions for the preparation of trans-2-aminocyclohexanol by ammonolysis of 1,l2-epoxycyclohexane or trans-2-bromocyclohexanol are realized by use of a 20-fold excess of aqueous alcoholic ammonia at 100 degrees. Under these conditions formation of secondary amines is minimized. Lower ammonia-reactant ratios, or the use of absolute methanolic ammonia or aqueous ammonia, lead to lower yields of primary amine and higher yields of secondary amines. 1-2-Epoxycylohexane has been isolated from the interaction of trans-2-bromocyclohexanol with aqueous ammonia. The oxide reacts more rapidly with aqueous alcoholic ammonia than the bromohydrin and the rate of conversion of the latter to amine is thus controlled by the rate of conversion of bromohydrin to oxide.
Report Number
DRCL-220 — Reprint; Previously accessioned as DSIS 58/08880
Date of publication
15 Jul 1957
Number of Pages
10
Reprinted from
Canadian J of Chemistry, vol 36, 1958, p 220-227
DSTKIM No
92-03696
CANDIS No
127046
Format(s):
Hardcopy;Originator's fiche received by DSIS

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