Acetic Acid → Tridec-4-en-1-yl acetate

HRID 1734298Notes

Reaction equation

HRID 1734298 reaction equation
[CH2:1](Cl)[CH2:2][CH2:3]/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(Cl)CC/C=C\CCCCCCCC.[C:29]([O-:32])(=[O:31])[CH3:30].[K+].C(O)(=O)C>>[C:29]([O:32][CH2:1][CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:31])[CH3:30]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 517044Potassium AcetateHCID 10856915HCID 10856915, compoundHCID 10932868HCID 10932868, compound

Product 1

HCID 62236Tridec-4-en-1-yl acetate

Procedure

495 g (2.2 moles) of the mixture of trans-4-tridecenyl chloride and cis-4-tridecenyl chloride synthesized in Example 1, 432 g (4.4 moles) of potassium acetate, and 264 g (4.4 moles) of acetic acid were mixed under an atmosphere of nitrogen (N2) and stirred at 180°-185° C. for 10 hours. Thereafter, this mixture was washed with 600 g of purified water and then with 600 g of a 5% aqueous solution of sodium bicarbonate. The resulting organic layer was purified by distillation. Thus, there was obtained 548 g (2.2 mole) of 4-tridecenyl acetate having a trans to cis ratio of 78:22 and a purity of 98%. This product is a sex pheromone component of the tomato pinworm (Keiferia lycopersicella) known as an insect pest of tomato fields principally in the United States of America.

Workup

  1. washThereafter, this mixture was washed with 600 g of purified water
  2. distillationThe resulting organic layer was purified by distillation

Sources & evidence

ORD record
ord-66e723b95b1845aca956aa74b657faa9
Source dataset
uspto-grants-1996_07
Patent number
US05532421

Reaction notes

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