New diarylmethane derivatives

摘要

The invention comprises 2 : 21-dihydroxy-5 : 51-dimethyldiphenylmethanes having in the 3-position a tertiary alkyl group of 4-8 carbon atoms attached at the tertiary carbon atom, and in the 31-position a cyclohexyl, bornyl, isobornyl or non-tertiary alkyl group of 1-5 carbon atoms. The group in the 31-position is suitably a methyl group. The compounds are made by reacting two substituted cresols of the general formul and in which R1 is a tertiary alkyl group of 4-carbon atoms attached at a tertiary carbon atom, R2 is a cyclohexyl, bornyl, isobornyl or non-tertiary alkyl group of 1-5 carbon atoms and X is in one component a hydrogen atom and in the other either a -CH2OH or -CH2Cl group. More particularly, they may be made by reacting a substituted cresol of one of the above general formul in which X is a hydrogen atom with formaldehyde in the presence of a basic compound as a catalyst to produce a cresol in which X is -CH2OH; or by reacting such a cresol in which X is a hydrogen atom with formaldehyde in the presence of anhydrous hydrogen chloride to produce a cresol in which X is -CH2Cl, and reacting either of these products with the other component cresol of the above general formula, where X is a hydrogen atom. In examples: (1) 2 : 4-dimethylphenol is treated with formaldehyde in the presence of calcium hydroxide to give 2-hydroxy-3 : 5-dimethylbenzyl alcohol which is heated with 2-tert.-butyl-4-methylphenol to give 2 : 21 - dihydroxy - 3 - tert. - butyl - 31 : 5 : 51 - trimethyldiphenylmethane; (2) 2-tert.-butyl-4-methylphenol is treated with 2-hydroxy-3 : 5-dimethylbenzyl chloride to give the product of (1), a similar method may be used to prepare the corresponding 3-tert.-amyl compound; (3) 2 - (1 : 1 : 3 : 3 - tetramethylbutyl) - 4 - methyl-phenol is treated with 2-hydroxy-3 : 5-dimethylbenzyl alcohol to give 2 : 21-dihydroxy-3-(1 : 1 : 3 : 3 - tetramethylbutyl) - 31 : 5 : 51 - tri methyldiphenylmethane; (4) 2-tert.-butyl-4-methylphenol is reacted with formaldehyde and the resulting 2-hydroxy-3-tert.-butyl-5-methylbenzyl alcohol is treated with 2-cyclohexyl-4-methylphenol to give 2 : 21-dihydroxy-3-tert.-butyl - 31 - cyclohexyl - 5 : 51 - dimethyldiphenylmethane; (5) 2-sec.-butyl-4-methylphenol is reacted with formaldehyde and the resulting 2 - hydroxy - 3 - sec. - butyl - 5 - methylbenzyl alcohol is treated with 2-tert.-butyl-4-methylphenol to give 2 : 21 - dihydroxy - 3 - tert. - butyl - 31 - sec. - butyl - 5 : 51 - dimethyldiphenylmethane; and (6) 2-hydroxy-3-tert.-butyl-5-methylbenzylalcohol is treated with 2-isobornyl-4-methylphenol to give 2 : 21-dihydroxy-3 - tert. - butyl - 31 - isobornyl - 5 : 51 - dimethyl diphenylmethane.