Organic Lab Reactions 218

Organic Lab Reactions 218 - 2-one-l J-Menthen-4-one-3...

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REDUCTION OF KETONES 213 TABLE II— Continued** REDUCTION OF KETONES WITH ALUMINUM ISOPROPOXIDE Compound Reduced 4'-Keto-l ',2',3',4'-tetra- hydro-3,4-benzpyrene 4'-Keto-l'-methyl-l',2',- 3',4'-tetrahydro-3,4«- benzpyrene 4-Keto-2'-methyl-l ',2',- 3',4'-tetrahydro-3,4- benzpyrene 4'-Keto-3'-methyl-l ',2',- 3',4'-tetrahydro-3,4- benzpyrene 6'-Keto-4',5-dimethyl- ene-1 ',2',3',4'-tetrahy- dro-3,4-benzpyrene 7-Cholestanone Norlupanone » Product Formed 4'-Hydroxy-l',2',3',4'- tetrahydro-3,4-benz- pyrene 4'-Hydroxy-l '-methyl- l',2',3',4'-tetrahydro- 3,4-benzpyrene 4'-Hydroxy-2'-methyl-l ',- 2',3',4'-tetrahydro-3,4- benzpyrene 4'-Hydroxy-3'-methyl- l',2',3',4'-tetrahydro-3,- 4-benzpyrene 6'-Hydroxy-4',5-dimeth- ylene-l',2',3',4'-tetra- hydro-3,4-benzpyrene 7-Cholestanol Norlupanol Reagent and Solvent * D C C C u D Yield 78-90% 91% 100% 94% 98% 16% Refer- ence 31 80 80 80 "ill 112 73 (d) Unsaturated Alicyclic and Aromatic Ketones Cyclohexen-2-one-l 4-Isopropylcyclohexen-
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Unformatted text preview: 2-one-l J-Menthen-4-one-3 ftt-Menthen-8-one-2 Z-Menthen-8-one-2 d-Menthen-4 (8)-one-3 d-Menthadien-6,8-one-2 4-Ketopinene Cyclohexen-2-ol-l 4-Isopropylcyclohexen-2-ol-l cis-and <rans-J-Menthen-4-ol-3 d2-Menthen-8-ol-2 Stereoisomers of menthen-8-ol-2 Menthadienes (43%) d-neo-menthen-8-ol-3 (5%) Stereoisomers of men-thadien-6,8-ol-2 4-Hydroxypinene U U D (t-C 3 H 7 OH) D (i-C 4 H 9 OH) D U D, U 49-74% 73-8% 84% 94% 48% 65-79% 113,114 92,115 24 24 116 116 28, 29, 30 3,63, 116,117 118 Nora: References 81-158 appear on pp ^221-223 * Unless otherwise stated, the reduotion was carried out with aluminum isopropoxide in boiling ISO-propyl alcohol solution C refers to clarified but undistilled aluminum uopropoxide; D, to distilled reagent; and U, to an untreated solution of the alkoxide (see p 199)...
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