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Derivate des Methylendioxybenzols, 24. Mitt.

Synthese des o-Safrols und des Myristicins

Derivatives of methylenedioxy-benzene, XXIV: Synthesis of o-safrole and of myristicine

  • Organische Chemie und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Zusammenfassung

Es wird die Synthese des isomerenfreien 2,3-Methylendioxyallylbenzols (o-Safrols) (1 d) durch Einwirkung von Chlorbrommethan auf 2,3-Dihydroxy-allylbenzol (1 b) beschrieben.

Durch Behandlung des 4-Hydroxy-3-methoxy-allylbenzols (3 a) mit Kaliumnitrosodisulfonat, Reduktion des entstehenden 3-Methoxy-5-allyl-o-benzochinons (4) mit Natriumdithionit und Methylenierung des 3-Methoxy-5-allyl-brenzcatechins (5) bildet sich Myristicin (3 b) in guter Ausbeute.

Abstract

Preparation of 2.3-methylenedioxy-allylbenzene (o-safrole) (1 d) free of isomers by reaction of 2.3-dihydroxy-allylbenzene (1 b) with CH2BrCl is described.

Treating 4-hydroxy-3-methoxy-allylbenzene (3 a) with potassium nitrosodisulfonate gives 3-methoxy-5-allyl-o-benzoquinone (4) which ist reduced to 3-methoxy-5-allyl-pyrocatechol (5) with sodium dithionite. Methylenation of3 c gives myristicin with good yield.

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Authors and Affiliations

  1. Institut für Organische Chemie der Technischen Hochschule Aachen, Aachen, Deutschland

    F. Dallacker & R. Sluysmans

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  1. F. Dallacker
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  2. R. Sluysmans
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Additional information

23. Mitt.:F. Dallacker, W. Edelmann undA. Weiner, Ann. Chem.,719, 112 (1968).

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Dallacker, F., Sluysmans, R. Derivate des Methylendioxybenzols, 24. Mitt.. Monatshefte für Chemie 100, 560–566 (1969). https://doi.org/10.1007/BF00904102

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  • DOI: https://doi.org/10.1007/BF00904102

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