194 REDUCTION WITH ALUMINUM ALKOXIDESOf these products the main one was the carbinol LXII. A similar oxideintermediate explains the formation of benzylmethylcarbinol froma-bromopropiophenone. In addition to the ethers corresponding to thesecarbinols, there was also obtained the monoether of a glycol. This mayhave been formed from the intermediate oxide (LVI) by the addition ofisopropyl alcohol to the oxide ring, or by direct reaction of the bromo-hydrin (LV) with aluminum isopropoxide. Curiously enough, when thereduction was carried out at 33°, a-bromoisobutyrophenone gave abromohydrocarbon as the main product.44This was shown to beLXIII accompanied by some of its allylic isomer (LXIV).OCHSCH3V - CH=C—CH2Br / \—CHBr—C=CH2LXIII LXIV LXVFrom 2-bromocyclohexanone (LXV), a 33% yield of cyclohexanolwas obtained in addition to a 30% yield of bromohydrin.46This reactionmay involve intermediates similar to those for a-bromoisobutyro-phenone.
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