2,6-bis(chloromethyl)-4-methylphenol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Bis(hydroxymethyl)-p-cresol (0.6779 g, 4.03 mmol) was suspended in CH2Cl2 (10 ml), and to this suspension was added slowly SOCl2 (3 ml, 41.1 mmol) under cooling in an ice-bath, and the resulting mixture was stirred at room temperature for 18 hours. The color of the reaction solution turned yellow. After completion of the reaction, the solvent was removed by evaporation to give 2,6-bis(chloromethyl)-p-cresol. under cooling in an ice-bath After completion of the reaction the solvent was removed by evaporation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At 0° C., 3.26 g (16 mmol) of 2,6-bischloromethyl4-methylphenol are added in portions to a solution of 5 g (32 mmol) of 1,4-dimethyl-1,4,7-triazacyclononane and 3.21 g (32 mmol) of triethylamine in 150 ml of methanol, and the mixture is stirred for 4 days at room temperature. For work-up, 1.28 g (32 mmol) of sodium hydroxide are added, and the sodium chloride which forms is filtered off. The solvent is removed under reduced pressure and the product is dried for one day under a high vacuum. Yield: 6.1 g (86%). Analysis: 1H-NMR:δ=2.24 (s,3 H, Carom.—CH3); 2.35 (s,12 H, N-CH3); 2.64 (m, 8 H, Carom.—CH2—N—CH2—CH2—N); 2.67 (s, 8 H, H3C—N—CH2—CH2—N—CH3); 2.87 (m, 8 H, Carom.—CH2N—CH2—CH2—N); 3.73 (s, 4 H, Carom.—CH2N); 6.82 (s, 2 H, Carom—H) 13C-NMR: 6=20.4 (Carom.—CH3); 45.4 (N—CH3); 53.0; 55.9; 56.2; (N—CH2—CH2—N); 58.6 (Carom.—CH2—N); 123.0 (Carom.—CH2—N); 127.4 (Carom.—CH3); 130.0 (Carom.—H), 154.7 (Carom.—OH) MS: (electrospray) m/e=447 (M+H⊕, 100%) the sodium chloride which forms is filtered off The solvent is removed under reduced pressure the product is dried for one day under a high vacuum