1-Hexene → 5-Decenoic acid

HRID 323914

Reaction equation

HRID 323914 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>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[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

5

Reactant 3

HCID 115971-HexeneHCID 153085-Hexenoic AcidHCID 38027Dec-5-enyl acetate

Product 1

HCID 534008795-Decenoic acid

Reagents, catalysts & solvents 1

HCID 178479819HCID 178479819, compoundCatalyst

Procedure

FIG. 6 shows an alternative synthesis of 5-decenyl acetate, in which 1-hexene is reacted with 5-hexenoic acid in the presence of Grubbs' catalyst 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-adf99e6f273840459f17678167ea6b71
Source dataset
uspto-grants-2001_04
Patent number
US06215019B1

Linked notes

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