Process for producing 6-hydroxy-2-naphthones

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

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C07C 4554

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active

046754490

ABSTRACT:
A process is provided for the production of 6-hydroxy-2-naphthones, e.g., 6-hydroxy-2-acetonaphthone, by contacting a 2-naphthyl carboxylate ester, e.g., 2-naphthyl acetate with at least 20 moles of hydrogen fluoride per mole of 2-naphthyl ester, at reaction temperatures, e.g., 0.degree. to 100.degree. C. for a period of reaction, e.g., 30 minutes to 8 hours sufficient to produce the desired amount of 6-hydroxy-2-naphthone. The process may utilize a carboxylic acid or anhydride, e.g., acetic acid or anhydride as an additive for the purpose of further increasing the regioselectivity of the 6-hydroxy-2-naphthone product. The process is capable of being carried out at a conversion of 2-naphthyl ester of at least 90% and a regioselectivity to 6-hydroxy-2-naphthone of at least 90 mol %.

REFERENCES:
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Simons et al., J.A.C.S., vol. 62, pp. 485-486 (1940).
Joshi et al, J. Indian Chem. Soc., vol. 29, pp. 225-232 (1952).

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