1,5-Hexadien-3-ol → HCID 12525557, compound

Reaction equation

[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]

Participants

Reactant 3

HCID 791221,5-Hexadien-3-ol

HCID 53527984,7-Octadienoic acid, ethyl ester

HCID 21226445Aluminium lithium hydride

Product 1

HCID 12525557HCID 12525557, compoundYield 92%

Procedure

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).

Sources & evidence

ORD record: ord-5fbad5f337ea45f09f9ac5d3d611582e
Source dataset: uspto-grants-1981_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04293674

Reaction notes

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