Acetate → 1-Chloro-5-decene

HRID 1416984Notes

Reaction equation

HRID 1416984 reaction equation
C(O[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14])(=O)C.C(O)CCCC=CCCCC.C([O-])(=O)C.[Cl:30]CCCCC=C.C=CCCCC>>[Cl:30][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 5

HCID 175AcetateHCID 115971-HexeneHCID 38027Dec-5-enyl acetateHCID 702336-Chloro-1-hexeneHCID 92458E-5-Decen-1-ol

Product 1

HCID 30855701-Chloro-5-decene

Procedure

Peach Twig Borer (PTB) pheromone is a mixture of 5-decenyl acetate and 5-decenol of approximately 85:15 molar ratio of the acetate to the alcohol. The synthesis of PTB pheromoneqcouples 1-chloro-5-hexene and 1-hexene to yield 1-chloro-5-decene. 1-chloro-5-decene is converted to 5-decenyl acetate, isomerized and a portion of the acetate is hydrolyzed to the corresponding alcohol to yield PTB pheromone. The overall scheme using the catalyst of Example 1 is shown below, followed by details of the synthesis. ##STR1##

Sources & evidence

ORD record
ord-0baa56873c364be08c9a01cfe82c6012
Source dataset
uspto-grants-1999_06
Patent number
US05916983

Reaction notes

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