GB870097A - Diethinyl-quinols and a process for their manufacture - Google Patents

Abstract

The invention comprises diethinyl quinols of the formula: <FORM:0870097/IV (b)/1> <FORM:0870097/IV (b)/2> where R1, R2, R3, R4 each represent a hydrogen or halogen atom or an alkyl group or two of the symbols R1, R2, R3, R4 together for part of one or more fused 6 membered ring systems, and R5 and R6 each represent a hydrogen atom or a hydrocarbon radical which may be interrupted by one oxygen atom. The quinols may be prepared by reacting the appropriate ortho or para quinone with an appropriate mono-substituted acetylene or the appropriate mono-substituted acetylene in liquid ammonia below 0 DEG C., preferably at -60 DEG to -30 DEG . The reaction may be carried out by adding the solid quinone or a solution of the quinone in an organic solvent to an ammoniacal solution of the alkali metal acetylide while passing a stream of acetylene through the solution. The examples describe the preparation of 1,4-diethinyl- 1,4-dihydroxycyclohexadiene-2,5; 2,3,5,6-tetrachloro-1,4-diethinyl-1,4-dihydroxy-cyclohexadiene-2, 5; 1,4-diethinyl-1,4-dihydroxy-1,4-dihydronaphthalene; 9,10-diethinyl-9,10-dihydroxy-9,10-dihydroanthracene; 6, 13-diethinyl-6,13-dihydroxy- 6,13-dihydropentacene; 9,10-diethinyl-9,10-dihydroxy-9,10-dihydrophenanthrene; p 1,4-di-(phenylethinyl)-1,4-dihydroxy-cyclohexadiene-2,5; 1,4-dihydroxy-1, 4-bis-[4-methoxy-butene-3-ine-1-yl]- cyclohexadiene-2,5; 1,4-dihydroxy-1,4-bis-[3-methoxy-propine-1-yl]-cyclohexadiene-2,5; and 1,4-dihydroxy-1,4-bis-[butene-3-ine-1-yl]- cyclohexadiene-2,5.