[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7](OCC)(=[O:15])[CH2:8][CH2:9]/[CH:10]=[CH:11]/[CH2:12][CH:13]=[CH2:14].C=CC(O)CC=C>>[CH2:7]([OH:15])[CH2:8][CH2:9]/[CH:10]=[CH:11]/[CH2:12][CH:13]=[CH2:14]trans-4,7-Octadienol (bp 100°-102° C./20 mm) was prepared in 92% yield by lithium aluminum hydride reduction of ethyl trans-4,7-octadienoate, which was prepared in 87% yield via the Claisen orthoester rearrangement of 1,5-hexadien-3-ol by the method of Johnson et al., J. Am. Chem. Soc., 92, 741 (1970).
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