Organic Lab Reactions 215

Organic Lab Reactions 215 - Camphor...

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210 REDUCTION WITH ALUMINUM ALKOXIDES TABLE II— Continued REDUCTION OF KETONES WITH ALUMINUM ISOPROPOXIDE Compound Reduced 1-Propionylnaphthalene 2-Propionylnaphthalene 1-Benzoylnaphthalene 2-Acetylfluorene 2-Acetylphenanthrene 3-Acetylphenanthrene 2-Phenanthreheacetone 9-Benzoylphenanthrene 2-Acetyldibenzothio- phene 3-Acetylpyrene Product Formed Ethyl-1-naphthylmeth- anol Ethyl-2-naphthylmeth- anol Phenyl-1-naphthylmeth- anol Methyl-2-fluorenylmeth- anol Methyl-2-phenanthryl- methanol Methyl-3-phenanthryl- methanol l-(2'-Phenanthryl-) pro- panol-2 Phenyl-9-phenanthryl- methanol Methyl-2-dibenzothienyl- methanol Methyl-3-pyrenylmeth- anol Reagent and Solvent * D D D D U u U,D U TJ U Yield . , „ 90% (crade) 100% 78% 95% 90% 88% 93% 68% 87% Refer- ence 86 86 36 36 87 88 89 90 91 80 (c) Alicylic Ketones Cyclopentanone Cyclohexanone Methylcyclohexanones 4-Isopropylcyclohex- anone Z-Menthone Sabina ketone
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Unformatted text preview: Camphor 2-Morpholinomethyl-cyclohexanone « 4-Methyl-2-morpholino-methylcyclohexanone Cyclopentanol Cyclohexanol Methylcyclohexanols as (5%) and trans (95%) 4-Isopropylcyclohex-anols Z-Menthol and neo-menthol Little reduction Borneol and isoborneol 2-Morpholinomethyl-cyclohexanol 4^Methyl-2-morpholino-methylcyclohexanol C C C U C,D (i-CHrOH) C r> D 33% 95% 90-95% — 90-99% — 100% 50% 83% 5 5 5 92,93 5,94 25 5 95 95 NOTE: References 81-158 appear on pp. 221-223. * Unless otherwise stated, the reduction was carried out with aluminum isopropoxide in boiling iso-propyl alcohol solution. C refers to clarined but undistilled aluminum isopropoxide; D, to distilled reagent; and TJ, to an untreated solution of the alkoxide (see p. 109)....
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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