Methoxyphenyl -6-phenyl-4-pyrone

2-(/ -METHOXYPHENYL)-6-PHENYL-4-PYRONE [4H-Pyran-4-one, 2-( -methoxyphenyl)-6-phenyl-] 

Submitted by Marion L. Miles and Charles R. Hauser 1 Checked by Victor Nelson, Wayland E. Noland, and William E. Parham 

In a 50-ml. Erlenmeyer flask is placed 10 ml. of concentrated (36N) sulfuric acid (Note 1), and the flask is then immersed in 

Regular commercial grade of concentrated sulfuric acid (sp. gr. 1.84) obtained from the General Chemical Division of Allied Chemical Corporation was used. 

For the preparation of this compound see Org. Syntheses, this volume, p. 57. 

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The method is an adaptation of the procedure of Light and Hauser.2 2-( -Methoxyphenyl) -6-phenyl-4-pyrone has been prepared in 50% yield by a Claisen-type acylation of -methoxy-acetophenone with ethyl phenylpropiolate accompanied by cyclization.3... 

The method described is that of Miles, Harris, and Hauser2 and is an improvement over the earlier procedure of Hauser and co-workers.3,4 In the earlier method the dianion of benzoylacetone, formed by the action of alkali amide in liquid ammonia, was treated with methyl anisate to yield 1 -(/>-methoxyphenyl)-5-phenyl-l,3,5-pentanetrione (61% based on the ester). This compo ir d has also been prepared by the base-catalyzed ring opening of 2 - f -mcthoxyphenyl) -6-phenyl -4 pyrone however, no yield is reported.5... 

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