Patent GB-1451118-A (GB)
Title: Process for the production of hydroxyalkylphenyl derivatives
IPC: C07B61/00
Filed: 1973-12-27
Abstract: 1451118 Preparation of alkylphenol derivatives CIBA-GEIGY AG 27 Dec 1973 [27 Dec 1972] 59769/73 Heading C2C Compounds of the formulµ wherein R 1  and R 2  independently of each other represent an alkyl group having from 1 to 6 carbon atoms, B 1  represents -O-(C x H 2x )-H or wherein x has a value from 6 to 30, inclusively, Y 1  represents an alkyl group having from 1 to 18 carbon atoms or a cycloalkyl group having from 3 to 12 carbon atoms and Y 2  represents hydrogen, an alkyl group having from 1 to 18 carbon atoms, or a cycloalkyl group of 5 to 12 carbon atoms, or Y 1  and Y 2  together with the nitrogen atom to which they are linked form a piperidino or piperazino ring, B 2  each represent -O- or -NH- and y has a value from 2 to 18, inclusively, and B 3  represents -O-CH 2 - and B 4  represents or wherein R 1  and R 2  are as defined above, and n is 0 to 6, or B 3  represents -NH-(CH 2 ) m -, wherein m has a value from 2 to 6, inclusively, and B 4  represents wherein p and q have values from 2 to 6, inclusively, and R 1  and R 2  are as defined above, or B 3  represents -NH-(CH 2 ) s -, wherein s has a value from 1 to 6, inclusively, and B 4  represents  wherein r has a value from 1 to 6 and R 1  and R 2  are as defined above and each of z and z<SP>1</SP> have a value from 2 to 12, inclusively, are obtained by gradually adding methyl acrylate to a phenol compound of the formula wherein R 1  and R 2  are as defined above, said addition being carried out at a constant slow rate throughout the reaction, so that the overall molar ratio of methyl acrylate and the phenol is at least 1 : 1; in the presence of from 0.001 to 10 mole per cent, based on the phenol compound of Formula V, of an alkaline catalyst, an alkaline catalyst selected from alkali metal hydrides, alkali metal alkoxides of the formula wherein M is an alkali metal, and X 1 , X 2  and X 3  are H, alkyl, aryl or aralkyl groups having up to 12 C atoms, and alkali metal amides of the formula wherein X 4  and X 5  are H alkyl or aryl having up to 12 C atoms and, immediately after completion of the reaction, adding to the resultant reaction mixture a compound selected from (a) a monohydric alcohol or a monoamine of the formulµ (b) a dihydric alcohol or a diamine of the formulµ (c) a tri- or tetrahydric alcohol or a polyamine of the formulµ and (d) a thioether compound of the formula wherein Y 1 , Y 2 , x, y, z and z<SP>1</SP> are as defined above and B 3  represents -O-CH 2 - and B 4 <SP>1</SP> represents or B 3  represents -NH-(CH 2 ) m -, wherein m has the value from 2 to 6, inclusively, and B 4 <SP>11</SP> represents or or B 3  represents -NH-(CH 2 ) s -, wherein s has the value from 1 to 6 and B 4 <SP>11</SP> represents and n, o, p and v are defined as above the second reaction being carried out at 130‹ to 160‹ C. in the presence of from 0.001 to 10 mole per cent based on the phenol compound of Formula V of a second alkaline catalyst selected from the alkaline catalysts specified above, but which is different from the catalyst employed in the first step, or alkali metal hydroxides. The products may be used for the stabilization of organic materials normally subject to oxidative deterioration.