1-(chloromethyl)-4-methylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 4-(5-methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide (3.14 g, 0.01 mol) and potassium carbonate (5.53 g, 0.04 mol) in DMF (50 mL) was stirred at room temperature for 5 hours. 4-methylbenzylchloride (3.45 g, 0.022 mol) was then added and the resulting mixture was stirred overnight. Ethyl acetate (50 mL) and sat. water (100 mL) were then added and the layers were separated. The organic layer was washed with NaHCO3 (50 mL), brine, 1 N HCl (25 mL) and water (2×25 mL). Then the organic layer was then dried over MgSO4, filtered and concentrated under vacuum. The resulting product was crystallized from boiling ethanol to afford 5.2 g of the product as a white solid: mp, 133.8-135.2° C. the resulting mixture was stirred overnight the layers were separated The organic layer was washed with NaHCO3 (50 mL), brine, 1 N HCl (25 mL) and water (2×25 mL) Then the organic layer was then dried over MgSO4 filtered concentrated under vacuum The resulting product was crystallized

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

Procedure: A glass-made reactor was charged with 5.1 g (0.02 mole) of 5-(α, α-dimethylbenzyl)salicylic acid, 50 ml of nitromethane, and as a catalyst, 1.4 g of anhydrous zinc chloride. The resultant mixture was maintained at 95° C. under stirring. At the same temperature, 22.5 g (0.16 mole) of p-methylbenzyl chloride was added dropwise over 10 hours to conduct a reaction. After completion of the dropwise addition, the reaction mixture was aged for 2 hours at the same temperature to complete the reaction. The weight average molecular weight of the thus-obtained resin was 2400. a reaction After completion of the dropwise addition the reaction

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

Procedure: The product is produced as described in example 1 from 0.72 g of NaH (80% suspension in mineral oil), 7 g. of 8-(2-oxo-benzimidazolin-1-yl)-caprylic acid methyl ester, 100 cc. of DMF, 3.4 g. of 4-methylbenzylchloride and 0.72 g. of NaJ. Eluant for chromatographic purification: hexane/ethylacetate. The product is produced Eluant for chromatographic purification