Robinson Annulation Mechanismbetween 2 Methylcyclohexene And Methyl Vinyl Ketone

2 methylcyclohexanone exists as a liquid slightly soluble in water and an extremely weak basic essentially neutral compound based on its pka.

Robinson annulation mechanismbetween 2 methylcyclohexene and methyl vinyl ketone.

2 methylcyclohexanone also known as fema 3946 or tetrahydro o cresol belongs to the class of organic compounds known as cyclic ketones. Packaging 1 kg in glass bottle 100 g in glass bottle other notes download our flavors and fragrances catalog to view our entire product line. 3 methyl 2 cyclohexen 1 one exists as a solid slightly soluble in water and an extremely weak acidic. 1 michael addition 2 intramolecular aldol condensation.

The first step in the process is the michael addition to an α β unsaturated ketone such as methyl vinyl ketone ethyl vinyl ketone is shown above. Michael addition of cyclohexanones to methyl vinyl ketone followed by intramolecular aldol condensation to afford six membered α β unsaturated ketones. In a second step the methyl group adjacent to the carbonyl is deprotonated and undergoes an. The reaction involves two important steps.

The journal of organic chemistry 45 p. The optimized procedure 6 2 methyl 2 3 oxobutyl 1 3 cyclohexanedione 3 is prepared by heating 2 methylcyclohexane 1 3 dione 2 with methyl vinyl ketone 1 in aqueous acetic acid at 75 c for 1 h after which 3 is purified. Mechanism of the robinson annulation. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

As illustrated in the following figure the robinson annulation reaction involves two steps the first step involves the michael addition of a ketone enolate the enolate derived from cyclohexanone in the example pictured below to an alpha beta unsaturated ketone methyl vinyl ketone below. The newly formed enolate intermediate must first tautomerize for the conversion to continue. 2 methylcyclohexanone is a cyclic ketone that is reported to occur in mint and horse chestnut. Pubmed the action of t butyl hypochlorite on 1 methyl 4 isopropyl 3 cyclohexene p menthene 3.

The annulation reaction has as its most common substrates generally cycle hexanone and methyl vinyl ketone. Cyclohexenones are compounds containing a cylohexenone moiety which is a six membered aliphatic ring that carries a ketone and has one endocyclic double bond. The cyclodehydration of 3 catalyzed by l proline is then performed at 25 c by simple stirring under argon for 120 h.