GB478571A - Manufacture of phenolic compounds containing a chloromethyl group and nitrogen-containing condensation products therefrom - Google Patents

Abstract

Phenols substituted in the nucleus by one or more aliphatic hydrocarbon chains of at least four carbon atoms are converted into chloromethyl derivatives by reaction with a solution of formaldehyde saturated with hydrogen chloride. The chloromethyl compounds may then be condensed with primary, secondary or tertiary amines, which may contain acidic groups, particularly sulphonic groups. The chloromethyl compounds are useful as intermediates for textile adjuvants, dyes, synthetic resins and tanning agents. The condensation products of the chloromethyl compounds with amines are useful as assistants in dyeing and as fungicides and insecticides. In the examples: (1) isobutylphenol is treated with a paraformaldehyde solution saturated with hydrogen chloride, and the chloromethyl compound so obtained is treated with pyridine; (2) dodecylphenol is converted as in example 1 into a chloromethyl derivative, and the latter is treated with pyridine; (3) isooctylphenol is converted as in example 1 into a chloromethyl derivative, and the latter is treated with pyridine; (4) chloromethyldodecylphenol is treated with triethylamine; (5) diisooctylphenol is converted as in example 1 into a chloromethyl derivative, and the latter is treated with pyridine; (6) chloromethyldodecylphenol is treated with methylaniline or (example 7) with aniline; (8) chloromethylisooctylphenol is condensed with sodium sulphanilate; (9) a mixture of isododecyl-, isotridecyl- and isotetradecyl-phenols is converted as in example 1 into a mixture of chloromethyl derivatives, and the latter is treated with pyridine, quinoline, trimethylamine or dimethylaniline. Specification 347,887 is referred to.