1-Hexene → 5-Decenoic acid

HRID 2122090Notes

Reaction equation

C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14])(=O)C.C=CCCCC.C(O)(=[O:27])CCCC=C>>[C:5]([OH:4])(=[O:27])[CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

Reactant 3

HCID 115971-Hexene

HCID 153085-Hexenoic Acid

HCID 38027Dec-5-enyl acetate

Product 1

HCID 534008795-Decenoic acid

Procedure

FIG. 12 shows an alternative synthesis of 5-decenyl acetate, in which 1-hexene is cross-metathesized with 5-hexenoic acid to produce 5-decenoic acid that can be recrystallized, reduced to an alcohol, and acetylated to yield a greater than 90% E-5-decenyl acetate.

Sources & evidence

ORD record: ord-a9a63450233141fa9dee09d58d86160b
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696597B2

Reaction notes

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