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Synthesis 1985; 1985(9): 876-878
DOI: 10.1055/s-1985-31368
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Hydroxymethylation of 2-Hydroxypropiophenones in Aqueous Medium: Synthesis of 3-Hydroxymethyl-3-methyl-4-chromanones and Their Conversion to 3-Methyl-4-chromanone-3-acetic Acids

Daniela Barlocco* , Giorgio Cignarella, Maria Michela Curzu
  • *Istituto Chimico Farmaceutico, Universitá di Milano, Viale Abruzzi 42, I-20131 Milano, Italy
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Publikationsdatum:
27. September 2002 (online)

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Reaction of o-hydroxypropiophenone (1a) with aqueous formaldehyde in sodium hydroxide solution led to the mono-hydroxymethylated 2a and/or the bis-hydroxymethylated derivative 3a, as well as to 3-methyl-4-chromanone (4a) and/or 3-methyl-3-hydroxymethyl-4-chromanone (5a), according to the ratio of the reagents employed. The mechanism of formation of 5a from 1a was also demonstrated. Compound 5a and its 6-chloro derivative 5b, similarly prepared from 5-chloro-2-hydroxypropiophenone (1b), were converted by standard procedure to the corresponding 3-methyl-4-chromanone-3-acetic acids 8a, b.

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