Organic Lab Reactions 217

Organic Lab - 5-Hydroxy-7-methyl-5,6-7,S-tetrahydro-l,2-beiu-anthracene 5-Hydroxy-8-methyl-6-6,7,8-tetrahydro-l,2-benzanthracene

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212 REDUCTION WITH ALUMINUM ALKOXIDES- TABLE II— Continued REDUCTION OF KETONES WITH ALtrMimjM ISOPROPOXIDE Compound Reduced 4-Keto-l ,2,3,4-tetrahy- drochrysene 12-Keto-4,5-dimethyl- 46,5,6,106,11,12-hexa- fiydrochrysene 7-Keto-4,5-methylene- 7,8,9,10-tetrahydro- chrysene 5-Keto-5,6,7,8-tetrahy- dro-l,2-benzan- thracene 5-Keto-6-methyl-5,6,7,- 8-tetraEydro-l ,2-benz- anthracene 5-Keto-7-methyl-5,6,7,8- tetrahy dro-1,2-benz- anthracene 5-Keto-8-methyl-5,6,7,- 8-tetrahydro-l ,2-benz- anthracene 6-Keto-l '-methyl-5,6,7,- 8-tetrahydro-l,2-benz- anthracene 8-Keto-7-methyl-5,6,7,- 8-tetrahydro-l,2-benz- anthracene 10-Keto-5,6,7,8,8o,9,10,- 10o-octahydro-l,2- benzanthracene 4o'-Keto-5,6,7,8,8a,9,- 10,10o-ootahydr6-4,- 10-ace-l,2-benzan- thracene Product Formed 4-Hydroxy-l ,2,3,4-tetra- hydroohrysene 12-Hydroxy-4,5-dimeth- yl-46,5,6,106,11,12- hexahydrochrysene 7-Hydroxy-4,6-methyl- ene-7,8,9,10-tetrahy- drochrysene 5-Hydroxy-6,6,7,8-tetm- hydro-1,2-benzan- thracene 6-Hydroxy-6-methyl-5,- 6,7,8-tetrahydro-l ,2- benzanthracene
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Unformatted text preview: 5-Hydroxy-7-methyl-5,6,-7,S-tetrahydro-l ,2-beiu!-anthracene 5-Hydroxy-8-methyl-6,-6,7,8-tetrahydro-l,2-benzanthracene 5-Hydroxy-l '-methyl-5 ,-6,7,8-tetrahydro-l,2-benzanthracene 8-Hydroxy-7-methyl-5,-6,7,8-tetrahydro-l ,2-benzanthracene 10-Hydroxy-5,6,7,8,8a,9,-10,10o-octahydro-l,2-benzanthracene 4a'-Hydroxy-6,6,7,8,8a,-9,10,10o-octahydro-4 r 10-ace-1,2-benaan-thracene Reagent and Solvent * U (I-CSHTOH) U (toluene) U (xylene) U — u 'V u u D U D D Yield 76% Dehy-dration — — 99% >90% 98% >79% 93% >89% 82% 97% Refer-ence 23 23 23 106 107 108 88 88 88 109 88 110 110 Nora: 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 refer* to clarified but undistilled aluminum isopiopojtide; D, to distilled reagent; and U, to an untreated solution of the alkoxide (see p. 190)....
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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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