METHOD OF PRODUCING ETHYL(2E,4Z)-5-CHLOROPENTA-2,4-DIENOATE Russian patent published in 2019 - IPC C07C69/65 C07C67/40 

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry, particularly to a method of producing ethyl(2E,4Z)-5-chloropenta-2,4-dienoate. Ethyl(2E,4Z)-5-chloropenta-2,4-dienoate is a promising starting compound in synthesis of practically important (2E,4Z)-dienic acids and derivatives thereof. Invention objective is to create a more efficient and safe method of producing ethyl(2E,4Z)-5-chloropenta-2,4-dienoate with higher output. Said problem is solved by the fact that in the method of producing ethyl(2E,4Z)-5-chloropenta-2,4-dienoate based on oxidation-olefination (2Z)-3-chloroprop-2-en-1-ol, according to the invention, the product is formed by single-reactor oxidation of (2Z)-3-chloroprop-2-en-1-ol under action of 2-iodooxybenzoic acid (IBX) to (2Z)-3-chloroprop-2-enal with subsequent olefination of the latter carbethoxymethylene)triphenylphosphorane in 1,2-dichloroethane at 50 °C for 4 hours.

EFFECT: main advantages of the method are higher output of product (70 % in terms of (2Z)-3-chloroprop-2-en-1-ol) and use of low-toxic IBX as an oxidising agent.

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