3613-55-6Relevant academic research and scientific papers
Experimental and theoretical investigations for the tandem alkylation-isomerization reactions between unsaturated carboxylic acids and allyl halides
Domingo, Luis R.,Gil, Salvador,Parra, Margarita,Sáez, José A.,Torres, Mercedes
, p. 6233 - 6239 (2003)
Alkylation of dienediolates from unsaturated carboxylic acids with allylic halides when followed by solventless thermal treatment at 150 to 200°C afford rearranged products on a trend highly dependent on the α carbon substitution. Thus, 2,2-bisallylated acids with H atoms at C-2 lead to its 1,3-shift, whereas 2-methyl-2,2-bisallylated acids lead to the corresponding Cope rearrangement product. In the latter case, this tandem allylation-Cope reaction lead, in a highly regio and diastereoselective way, to products not accessible from direct alkylation. B3LYP/6-31G* energies for the compounds involved at these isomerizations are in reasonable agreement with the experiments, allowing to explain the formation of the more stable product under thermodynamic equilibrations.
PROCESSES FOR PREPARING 2-ISOPROPENYL-5-METHYL-4-HEXENOIC ACID, 2-ISOPROPENYL-5-METHYL-4-HEXEN-1-OL, AND A CARBOXYLATE ESTER THEREOF
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Paragraph 0256-0258, (2021/10/22)
The present invention provides a process for preparing 2-isopropenyl-5-methyl-4-hexenoic acid of the following formula (4), comprising steps of: subjecting a Grignard reagent of the following general formula (1), wherein R1 represents a linear, branched, or aromatic monovalent hydrocarbon group having 1 to 8 carbon atoms, and X represents a chlorine atom, a bromine atom, or an iodine atom, and 1,1,1,3,3,3-hexamethyldisilazane to a deprotonation reaction to form a 1,1,1,3,3,3-hexamethyldisilazane derivative; and subjecting 2-methyl-3-buten-2-yl 3-methyl-2-butenoate of the following formula (3) to a rearrangement reaction in the presence of the 1, 1, 1,3,3,3-hexamethyldisilazane derivative to form 2-isopropenyl-5-methyl-4-hexenoic acid (4).
METHOD FOR PRODUCING (E)-2-ISOPROPYL-5-METHYL-2,4-HEXADIENYL ACETATE
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Paragraph 0106-0107, (2015/05/05)
Provided is a simple and efficient method for producing (E)-2-isopropyl-5-methyl-2,4-hexadienyl acetate. More specifically, provided is a method for producing (E)-2-isopropyl-5-methyl-2,4-hexadienyl acetate including the steps of: isomerizing 2-isopropenyl-5-methyl-4-hexenoic acid (1) into (E)-2-isopropyl-5-methyl-2,4-hexadienoic acid (2), reducing thus formed (E)-2-isopropyl-5-methyl-2,4-hexadienoic acid (2) into (E)-2-isopropyl-5-methyl-2,4-hexadienol (3), and acetylating thus formed (E)-2-isopropyl-5-methyl-2,4-hexadienol (3) into (E)-2-isopropyl-5-methyl-2,4-hexadienyl acetate (4), wherein Ac represents an acetyl group.
