Acetate → 1-Chloro-5-decene

반응식

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]

참가 물질

반응물 5

HCID 175Acetate

HCID 115971-Hexene

HCID 38027Dec-5-enyl acetate

HCID 702336-Chloro-1-hexene

HCID 92458E-5-Decen-1-ol

생성물 1

HCID 30855701-Chloro-5-decene

실험 절차

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##