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Organic Lab Reactions 199

Organic Lab Reactions 199 - 194 REDUCTION WITH ALUMINUM...

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194 REDUCTION WITH ALUMINUM ALKOXIDES Of these products the main one was the carbinol LXII. A similar oxide intermediate explains the formation of benzylmethylcarbinol from a- bromopropiophenone. In addition to the ethers corresponding to these carbinols, there was also obtained the monoether of a glycol. This may have been formed from the intermediate oxide (LVI) by the addition of isopropyl alcohol to the oxide ring, or by direct reaction of the bromo- hydrin (LV) with aluminum isopropoxide. Curiously enough, when the reduction was carried out at 33°, a-bromoisobutyrophenone gave a bromohydrocarbon as the main product. 44 This was shown to be LXIII accompanied by some of its allylic isomer (LXIV). O CH S CH 3 V - CH=C—CH 2 Br / \—CHBr—C=CH 2 LXIII LXIV LXV From 2-bromocyclohexanone (LXV), a 33% yield of cyclohexanol was obtained in addition to a 30% yield of bromohydrin. 46 This reaction may involve intermediates similar to those for a-bromoisobutyro- phenone.
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