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Organic Lab Reactions 213

Organic Lab Reactions 213 - or Methyl ester of...

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208 REDUCTION WITH ALUMINUM ALKOXIDES TABLE I—Continued REDUCTION OF ALDEHYDES WITH ALUMINUM ALKOXIDES Compound Reduced 4-Nitrobenzaldehyde 2-Nitro-3,4-dimethoxy- benz aldehyde Cinnamaldehyde a-Chlorocinnamaldehyde ot-Bromocinnamaldehyde 2-, 3-, or 4-Nitrocinnamal- dehyde a-M ethylcinnamaldehyde ll-Phenyl-2,4,6,8,10-un- decapentaenal-1 2-Styrylbenzaldehyde 2,3-Dimethyl-l-naph- thaldehyde 9-Pluorenealdehyde 3-Pyrenealdehyde Methyl ester of meao- pyropheophorbide b Methyl pheophorbide b Trimethyl ester of rho- dineffr Product Formed 4-Nitrobenzyl alcohol 2-Nitro-3,4-dimethoxy- benzyl alcohol Cinnamyl alcohol a-Chlorocinnamyl alcohol a-Bromocinnamyl alcohol 2, 3, or 4-Nitrocinnamyl alcohol a-Methylcinnamyl alco- hol ll-Phenyl-2,4,6,8,10-un- decapentaenol-1 2-Styrylbenzyl alcohol 2,3-Dimethyl-l-naph- thyhnethanol 9-Fluorylmethanol 3-Pyrenylmethanol' Methyl ester of meso- pyropheophorbide 6-3- methanol (15 minutes)
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Unformatted text preview: or Methyl ester of 9-hy-droxydesoxo-meso-pyropheophorbide 6-?-methanol (2 to 4 hours) Methyl pheophorbide b-3-methanol Trimethyl ester of rho-dine ^7-3-methanol Reagent and Solvent * R in A1(OR) 3 C 2 H 6 (25°) C2H5 i-C 3 H 7 t! 2 H 6 C 6 H 6 CH 2 C2S5 CJHB C2H5 i-C 3 H 7 ~i-C 3 H 7 (D) i-C 3 H 7 i-C 3 H 7 i-C 3 H 7 (D) i-C 3 H 7 i-C 3 H 7 (C) J-CSHTCC) ^•C 3 H 7 (C) j-C 3 H 7 (C) Yield 92% 92-97% 68-80% 45-86% 80% —. — — —-90% 95% — 50% 54% — — 50% xveter-ence 2 14 13,75 1,2,3 3,63 12 12 12 44 76 77 78 79 80 2 2 . 22-22 22 NOTE: References 69-80 appear on p. 221. * If no solvent is listed the alcohol corresponding to the alkoxide was used. C refers to clarified aluminum iaopropoxide but not distilled; D, to distilled reagent; and V, to an untreated solution of the alkoxide (see p. 199)....
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