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Organic Lab Reactions 226

Organic Lab Reactions 226

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REDUCTION OF KETONES 221 TABLE II— Continued REDUCTION OF KETONES WITH ALUMINUM ISOPBOPOXIDE Compound Reduced Dimethyl ester of 2,a- ketopheoporphyrin as Methyl ester of 2- desvinyl-2-acetyl- pheophorbide o Product Fonned Dimethyl ester of 2,a- hydroxypheoporphyrin 05 (main product) Methyl ester of 2,a-hy- droxymesopheo- phorbide a (main prod- uct) Reagent and Solvent * C C Yield Refer- ence 22 22 * Unless otherwise stated, the reductioa was oarried out with aluminum isopropoxide in boiling iso- propyl alcohol solution. C refers to clarified but undistilled aluminum isopropoxide; D, to distilled reagent; and U, to an untreated solution of the alkoxide (see p. 199). 69 E. E. Royals, private communication. 60 Dworzak, Monatsh., 47, 11 (1926). 6 1 1. G. Farbenindustrie A.-G., Ger. pat., 489,281 (Jan. 15, 1930) [Chem. Zenir. (I), 3104 (1930)]. 62 Reichstein, Ammann, and Trivelli, Heh. Chim. Ada, 15, 261 (1932). 63 Sachs, Perfumers' J., 7, No. 3, 11, 32 (1926) [C. A., 20, 2321 (1926)]. M French and Gallagher, J. Am. Chem. Soc, 64, 1498 (1942). 66 Jitkow and Bogert, J. Am. Chem. Soc, 63, 1981 (1941). 64 Blumenfeld, Ber., 74, 529 (1941). 67 Kuhn and Hoffer, Ber., 67, 358 (1934). 68 Kuhn and Wendt, Ber., 69, 1555 (1936). 69 Haworth, Heilbron, Jones, Morrison, and Polya, J. Chem. Soc., 1939, 128. 70 Krauze and Slobodin, J. Gen. Chem. U.S.S.R., 10, 907 (1940) [C.A., 35, 3237 (1941)].
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