24199-46-0

Usage

Synthesis Reference(s)

Tetrahedron, 25, p. 1667, 1969 DOI: 10.1016/S0040-4020(01)82740-X

InChI:InChI=1/C9H16O/c1-4-8(2)6-5-7-9(3)10/h6H,4-5,7H2,1-3H3

Upstream product

• 102540-62-5 acetoacetic acid-(1-ethyl-1-methyl-allyl ester) 
• 1937-03-7 3-methyl-2-pentenyl chloride 
• 141-97-9 ethyl acetoacetate 
• 5978-08-5 1-chloro-4-(1,3-dioxolane)-n-pentane 
• 78-93-3 butanone 
• 918-85-4 3-hydroxy-3-methyl-1-pentene 
• 116-11-0 2-Methoxypropene 

Downstream Products

• 61792-11-8 3,7-dimethylnona-2,6-dienenitrile 
• 1005418-58-5 3,7-dimethyl-3,6-nonadiene nitrile 
• 1108727-44-1 7-methyl-3-methylene-6-nonene nitrile 
• 925-69-9 6-Methyl-2-octanone 

Relevant academic research and scientific papers

NOVEL USE OF PHENYL PHOSPHINIC ACID

The present invention is directed towards a process for the manufacture of gamma, delta-unsaturated ketones of the general formula (III) by reacting a tertiary vinyl carbinol of the general formula (I) with an isopropenyl alkyl ether of the general formula (II) in the presence of a catalyst of the general formula (IV), wherein R1 and R6 are independently from each other methyl or ethyl, R3 is methyl, and R2 is a saturated or unsaturated linear, branched or cyclic hydrocarbyl group with 1 to 46 C atoms. The present invention is also directed towards the reaction mixture as such, i.e. the mixture of the compound of formula (I), the compound of formula (II) and the catalyst of formula (IV).

-SIGMATROPIC REARRANGEMENTS OF THE ACETOACETATES OF ALLYL ALCOHOLS (CARROLL REACTION) AND ALLYLPHENYL ETHERS (CLAISEN REACTION) ON THE SURFACE OF ADSORBENTS

A method has been developed for effecting rearrangements of allylacetoacetates to γ,δ-unsaturated ketones (Carroll rearrangement) and allylaryl ethers to the corresponding allylphenols (Claisen rearrangement) under conditions of adsorption on aluminum oxide and silica gel.The method provides a sharp reduction of the temperature of these reactions and improvement of their efficiency.

CARROL REARRANGEMENT ON THE SURFACE OF CHROMATOGRAPHIC GRADE ALUMINA

Thermolysis on the surface of AL2O3 is proposed as a mild and convenient preparative method for -sigmatropic Carrol rearrangement of acetoacetic esters of tertiary allyl alcohols into respective γ,δ-unsaturated ketones.