Organic Lab Reactions 212

Organic Lab Reactions 212 - zyl alcohol,...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
• REDUCTION OF ALDEHYDES 207 TABLE I— Continued REDUCTION OF ALDEHYDES WITH ALUMINUM ALKOXIDES Compound Reduced A 3 -3,4,6-Trimethyltetra- hydrobenzaldehyde A 3 -2,2,4-Trimethyltetra- hydrobenzaldehyde A 8 -2-Phenyltetrahydro- benzaldehyde A 8 -6-Phenyl-3,4-dimeth- yltetrahydrobenzalde- hyde Cyclocitral Axerophthal 5,5;9-Triinethyl-5,6,7,8,9,- 10-hexahydro-l-naph- thaldehyde Lupenal (a triterpene aldehyde) Furfural B.enzaldehyde 4-Chlorobenzaldehyde 4-Methoxybenzaldehyde 3-Methoxy-6-bromoben- zaldehyde 3,4-Methylenedioxyben- zaldehyde 3-Benzyloxy-4-methoxy- benzaldehyde 2-Nitrobenzaldehyde Product Formed A 3 -3,4,6-Trimethyltetra- hydrobenzyl alcohol A s -2,2,4-Trimethyltetra- hydrobenzyl alcohol A 8 -2-Phenyltetrahydro- benzyl alcohol s A 8 -6-Phenyl-3,4-dimeth- yltetrahydrobenzyl alcohol Cyclogeraniol Isomer of vitamin A (axerophthol) 5,5,9^11106^1-5,6,7,8,- 9,10-hexahydro-l-naph- thylmethanol Pseudolupenol Furfuryl alcohol Benzyl alcohol 4-Chlorobenzyl alcohol 4-Methoxybenzyl alcohol 3-Methoxy-6-bromoben-
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: zyl alcohol, 3,4-Methylenedioxyben-zyl alcohol 3-Benzyloxy-4-methoxy-benzyl alcohol 2-Nitrobenzyl alcohol Reagent and Solvent * R in A1(OR) 3 ^C 3 H 7 ;-C 3 H 7 (D) t-C s H 7 (D) i-C 3 H 7 t-C 3 H 7 (D) i-C 3 H 7 (D) i-C 3 H 7 (D) i-C 3 H 7 (D) C 2 H B (25) i-CsB. 7 (82) i-C 3 H 7 (D) i-C 3 H 7 (benzene) C 2 H 6 (benzene) C 2 H B C 2 H 6 (2S O ) C 2 H 6 (25) C 2 H 6 ^C 3 H 7 (D) i-C 3 H 7 (D) i-C 3 H 7 (C) C 2 H 6 Yield ' 70% 8P% 77-93% 66% 55% 88% 75% 89% 55% 28% 82-89% 92% 85% 88-100% (crude) 90% 93-98% 92% 100% ence 64 65 66 64 67,68 69,70 71 (cf. 72) 73 2 74 37 13 13 2, 12 2 2 16 47 48 5 14 NOTE: References 59-80 appear on p. 221. * If no solvent is listed the alcohol corresponding to the alkoxide was used C refers to clarified aluminum isopropoxide but not distilled; D, to distilled reagent; and U, to an untreated solution of the alkoxide (see p. 199)....
View Full Document

Ask a homework question - tutors are online