1-(bromomethoxy)octane

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

Procedure: 0.138 g (1 mmole) of 1,2-dimethoxybenzene (veratrol) were reacted with 0.223 g (1 mmole) of bromomethyl octylether in 5 ml 1,2-dichloroethane in the presence of 0.12 ml (1 mmole) SnCl4 at room temperature for 1 hour. After washing with HCl and water, followed by drying on Na2SO4 the product was isolated by the evaporation of the solvent. The product (0.275 g) corresponds by mp., NMR and analysis to cyclotriveratrylene (A. J. Lindsey. J. Chem. Soc. 1685 (1965) obtained by trimerization of 3-chloromethyl-1,2-dimethoxybenzene. After washing with HCl and water by drying on Na2SO4 the product was isolated by the evaporation of the solvent

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

Procedure: 30 g (1 mole) of paraformaldehyde, 107 ml of 1-octanol (1 mole) are stirred in 100 ml chloroform at 0°-5° C., by passing HBr gas. After the reaction completion, indicated by the complete dissolution of the solid, the organic layer is washed with water several times, and dried over anhydrous sodium sulphate. The residue is diluted in chloroform, to give a 3M solution. The product boiled at 150°-155° C. (1 torr) and has a singlet (2 hydrogens) at 5.8 ppm from TMS. The product is kept refrigerated. After the reaction completion, indicated by the complete dissolution of the solid the organic layer is washed with water several times dried over anhydrous sodium sulphate The residue is diluted in chloroform