Method of acylation of phloroglucinol

C - Chemistry – Metallurgy – 07 – C

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260/578, 260/582

C07C 49/21 (2006.01) C07C 45/46 (2006.01) C07C 45/68 (2006.01) C07C 45/71 (2006.01) C07C 49/825 (2006.01)

Patent

CA 1068725

ABSTRACT OF THE DISCLOSURE A process of acylation of phloroglucinol in the presence of a Friedel Crafts catalyst is provided, the process is effected in the presence of nitromethane and dichloromethane so as to produce an acylphloroglucinol. The acylphloroglucino is reacted with a compound selected fromy,y- dimethyl allyl bromide and 2 - methyl - but - 3 - ene - 2- ol in the presence of a weak Lewis acid and in an organic solvent to produce a 4 - desoxyhumulone which is then oxidised to produce a corresponding humulone. Thus, an improved process is now provided for the production of humulone, with the aid of which it is possible, starting with phloroglucinol, to produce humulone with a total yield such that the synthetic production of humulone is economically interesting in comparison with the production of humulone from natural hops.

251884

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