Patent GB-892261-A (GB)
Title: A process for the preparation of hydroxyphenyl substituted methanes
IPC: C08K5/13
Filed: 1960-07-28
Abstract: Resins may be obtained by reacting aldehydes or ketones with bis-phenols of the formula <FORM:0892261/IV (a)/1> where the R groups are the same or different alkyl groups having up to 8 carbon atoms and where at least one alkyl group ortho to each hydroxyl group is branched on the carbon atom bound to the ring and has at least 3 carbon atoms, Specification 806,961 is referred to.ALSO:A process for preparing a hydroxyphenyl substituted methane comprises reacting a 3,5-dialkyl-mono-hydroxybenzyl alcohol of the formula <FORM:0892261/IV (b)/1> where R1 is an alkyl group having between 3 and 8 carbon atoms inclusive and is branched on the carbon atom bound to the ring, and one of R2 and R3 is an alkyl group having up to 8 carbon atoms and the other is a hydroxymethyl group, with an alkyl phenol having the structure <FORM:0892261/IV (b)/2> where either (i) R4=R1, R5=R2, R6=R3; or (ii) any two of R4, R5 and R6 are hydrogen and the other is an alkyl group having up to 8 carbon atoms; or (iii) R4 is an alkyl group having between 3 and 8 carbon atoms inclusive and is branched on the carbon atom bound to the ring and one of R5 and R6 is an alkyl group having up to 8 carbon atoms and the other is hydrogen, in the presence of a solvent consisting essentially of a secondary or tertiary alcohol or a mixture thereof and in the presence of a catalytic amount of a base.  The structure of the product depends on the structure of reactants; thus when the two components are identical, i.e. self-condensation, the product is a 2,21- or 41,41-dihydroxy-tetraalkyl-diphenyl methane, when a monoalkyl phenol is used the product is a bis-(hydroxy-dialkylbenzyl)-monoalkyl phenol and when a dialkyl phenol is used the product is a 2,21-, 4,41- or 2,41-dihydroxy-tetra-alkyl-diphenyl methane.  The invention includes novel compounds of the formula <FORM:0892261/IV (b)/3> where the R groups are the same or different alkyl groups having upto 8 carbon atoms and where at least one of the alkyl groups ortho to each hydroxyl group is branched on the carbon atom bound to the ring and has at least 3 carbon atoms; <FORM:0892261/IV (b)/4> where R1, R2, R4 and R5 are alkyl groups having up to 8 carbon atoms, R1 and R4 having between 3 and 8 carbon atoms inclusive and being branched on the carbon atom bound to the ring and R4 and R5 are different from R1 and R2; <FORM:0892261/IV (b)/5> where R1 is an alkyl group having from 3 to 8 carbon atoms inclusive and is branched on the carbon atom bound to the ring and R2 and R6 are alkyl groups having up to 8 carbon atoms.  The reaction takes place by heating stoichio-metric proportions of reactants, e.g. at 50 DEG C.-100 DEG C. in alcohol which may correspond to the secondary or tertiary substituent on the reactants, e.g. tert.-butanol in the case of tert. butyl substituted phenols and benzyl alcohols, using up to about 1% by weight of base, e.g. KOH, K2CO3 or an organic base, based on the benzyl alcohol. Examples describe the preparation of the 3,5,31,51-tetra-t. butyl, 3,31-di-t. amyl-5,51-dimethyl, 3,31-di-isopropyl-5,51-dimethyl, 3,5-dimethyl-31,51-di-t. butyl, 3,31,5-tri-t. butyl-51-methyl and 3,5-di-isopropyl-31,51-di-t. butyl derivatives of 4,41-dihydroxy-diphenyl-methane, and of the 3,31,5,51-tetra-t. butyl derivatives of 2,21- and 2,41-dihydroxy-diphenyl-methane.  The 2,41-dihydroxy compounds may be reacted with epichlorhydrin to give monoglycidyl ethers.  Specification 806,961 is referred to.