Patent GB-1289041-A (GB)
IPC: C07C43/20
Filed: 1970-01-20
Abstract: 1289041 Preparation of 2-(6-methoxy-2- naphthyl)-propanol; organometallic compounds SYNTEX CORP 20 Jan 1970 [30 Sept 1969] 2766/70 Addition to 1271132 Headings C2C and C2J A process for preparing 2-(6-methoxy-2- naphthyl)-1-anol comprising one of the following procedures: A (a) reaction a borane compound selected from the group of compounds which can be represented by the formula wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> each is a 2-(6-methoxy- 2 - naphthyl) - 1 - propyl, alkyl, cycloalkyl or aralkyl group and at least one of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> is said 2-(6-methoxy-2-naphthyl)-1-propyl group, with hydrogen peroxide in an aqueous solution of an inorganic base until 2-(6-methoxy-2-naphthyl)propanol is formed; and (b) separating 2 - (6 - methoxy - 2 - naphthyl) - 1- propanol from the reaction mixture; B (a) reacting a compound having the Formula Ib where in M is MgCl, MgBr, MgI, Li, Na, K, Zn ¢  or Cd ¢ , with formaldehyde; (b) treating the reaction mixture with an acid until 2-(6- methoxy - 2 - naphthyl) - 1 - propanol is formed; and (c) separating 2-(6-methoxy-2- naphthyl)-1-propanol from the reaction mixture; C (a) reacting 2-methoxynaphthalene with propylene oxide in the presence of a Lewis acid in an inert organic solvent at -10‹ to 40‹ C. until 2 - (6 - methoxy - 2 - naphthyl) - 1 - propanol is formed; and (b) separating 2-(6- methoxy - 2 - naphthyl) - 1 - propanol from the reaction mixture; D (a) reacting 2-(6-methoxy-2-naphthyl)- propylene oxide with a metal hydride in the presence of a Lewis acid in an ether solvent until 2 - (6 - methoxy - 2 - naphthyl) - 1 - propanol is formed; and (b) separating 2-(6-methoxy-2- naphthyl)-1-propanol from the reaction mixture; E (a) treating 2 - (6 - methoxy - 2 - naphthyl)- 2 - propen - 1 - ol with hydrogen in the presence of a hydrogenation catalyst in an inert organic solvent until 2 - (6 - methoxy - 2- naphthyl) - 1 - propanol is formed; and (b) separating 2.- (6 - methoxy - 2 - naphthyl) - 1- prqpanol from the reaction mixture; F (a) treating 2-(6-methoxy-2-naphthyl)acrylic acid with diborane in an ether solvent until 2 - (6 - methoxy - 2 - naphthyl) - 1 - propanol is formed; and (b) separating 2-(6-methoxy-2- naphthyl)-1-propanol from the reaction mixture; and G (a) reacting 2-methoxynaphthalene with a compound having the formula wherein X<SP>1</SP> is chloro, bromo or iodo and R<SP>6</SP> is an alkyl, aryl or aralkyl group, in the presence of a Lewis acid in an inert organic solvent at - 10‹ to 40‹ C. until the corresponding 2-halo-1- propanol alkyl-, aryl- or aralkylcarboxylate is formed; (b) hydrolysing the ester group of the 2-halo-1-propanol alkyl-, aryl- or aralkylcarboxylate; and (c) separating 2-(6-methoxy- 2-naphthyl)-1-propanol from the reaction mixture. When dl-starting materials are used, the product may be resolved for example via the cinchonidine salt of the hemiphthalic acid ester prepared by reaction with phthalic anhydride. 2 - ( - 6 - Methoxy - 2 - naphthyl)propylene oxide is prepared by action of sodium methoxide and trimethylsulphonium iodide in dimethylsulphoxide on 2-acetyl-6-methoxynaphthalene prepared by action of acetyl chloride on 2-methoxynaphthalene. Organo-metal compounds of Formula Ib above wherein M is MgBr, Li or Zn, are prepared by action of Mg, Zn or Li on the compound wherein M is Br and the Grignard compound may be converted into compounds of Formula Ib wherein M is Cd, K or Na by action of cadmium chloride, K or Na.