Prepn. of 4:methoxyethyl phenol - from 4:hydroxy benzaldehyde and methoxymethyl magnesium halide

4-(2- Methoxyethyl) phenol (I) is prepd. by treating 4-hydroxy-benzaldehyde with a halide to form an aldehyde of formula (II) (where R is a gp. that is easily eliminated). Cpd. (II) is treated with methoxy methyl magnesium chloride to form 4-(1-hydroxy-2-methoxy ethyl) phenol (III). Cpd. (III) is th...

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Bibliographische Detailangaben
1. Verfasser: MICHEL BARON, MICHEL CHIGNAC, CLAUDE GRAIN ET CHARLES PIGEROL
Format: Patent
Sprache:eng ; fre
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Zusammenfassung:4-(2- Methoxyethyl) phenol (I) is prepd. by treating 4-hydroxy-benzaldehyde with a halide to form an aldehyde of formula (II) (where R is a gp. that is easily eliminated). Cpd. (II) is treated with methoxy methyl magnesium chloride to form 4-(1-hydroxy-2-methoxy ethyl) phenol (III). Cpd. (III) is then dehydrated to form the 2-methoxy vinyl cpd., and hydrogenated to the 2-methoxyethyl cpd. (IV) (where R' is R or H). If necessary R' is saponified to give (I). (I) is an intermediate for the preparation of metoprolol, a cardiovascular agent. L'INVENTION SE RAPPORTE A UN PROCEDE DE PREPARATION DE (METHOXY-2 ETHYL)-4 PHENOL DE FORMULE:(CF DESSIN DANS BOPI)CARACTERISE EN CE QUE L'ON FAIT REAGIR L'HYDROXY-4 BENZALDEHYDE AVEC UN HALOGENURE, PUIS L'ON CONDENSE L'ALDEHYDE OBTENUE SUR LE CHLORURE DE METHOXYMETHYLMAGNESIUM POUR FORMER L'ETHER DE L'(HYDROXY-1 METHOXY-2 ETHYL)-4 PHENOL QUE L'ON DESHYDRATE POUR FORMER L'ETHER DU (METHOXY 2 VINYL)-4 PHENOL ET ENFIN L'ON HYDROGENISE CE DERNIER COMPOSE POUR FORMER, APRES SAPONIFICATION EVENTUELLE, LE (METHOXY-2 ETHYL)-4 PHENOL.LE PRODUIT PREPARE SELON L'INVENTION EST UN PRODUIT DE DEPART POUR LA SYNTHESE DU METOPROLOL.