22911-69-9

Upstream product

• 23032-35-1 2-((1R,2S)-2-Dichloromethyl-2-methyl-5-oxo-cyclohex-3-enyl)-malonic acid dimethyl ester 

Downstream Products

• 136848-58-3 4-methyl-4-dichloromethyl-5-(methoxycarbonyl)methyl-6-trans-acetoxy-2-cyclohexen-1-one 
• 22910-46-9 4-methyl-4-dichloromethyl-5-(methoxycarbonyl)methyl-2-cyclohexen-1-one 

Relevant academic research and scientific papers

Microbiological degradation of a synthetic benzofurane type lactone

A benzofurane type lactone 4 incorporating an α-methylene-γ- butyrolactone moiety has been synthesized. The key steps involved are the Michael condensation of 4-dichloromethyl-4-methyl-2,5-cyclohexadienone 1 with dimethyl malonate and acetoxylation of 4-dichloromethyl-5-carboxymethyl-4- methyl-2-cyclohexenone 2 with lead (IV) acetate in BF3-etherate which are indicative of the general route to γ-lactone. Microbial degradations of the synthetic benzofurane type lactone 4 have also been studied using Aspergillus niger, Saccharomyces cerevisiae, Bacillus mycoides, Agrobacterium tumefaciens, Pseudomonas glicinea and Pseudomonas fluorescens. The lactone acts both as an additive for the nutrient substrate and as a source of organic carbon.

STEREOSPECIFIC ACETOXYLATION OF 4-METHYL-4-DICHLOROMETHYL-5-(METHOXYCARBONYL)METHYL-2-CYCLOHEXEN-1-ONE WITH LEAD(IV) ACETATE

Acetoxylation of 4-methyl-4-dichloromethyl-5-(methoxycarbonyl)methyl-2-cyclohexen-1-one with lead(IV) acetate in the presence of Lewis acids gives the corresponding 6-trans-α-acetoxylated derivative which, in an excess of boron trifluoride etherate (or in acidic media), undergoes cyclization to a trans-γ-lactone.