Chloromethyl Methyl Ether → HCID 67119201, compound

Participants

Reaction Steps

After trimethyl orthoformate (106 ml, 0.972 mol) and camphorsulfonic acid (0.751 g, 3.24 mmol) were added to a solution of 3-tert-butyl-2-hydroxybenzaldehyde (28.8 g, 162 mmol) which was synthesized according to the method described in literature (Hofsløkken, N. U. et al., Acta Chem. Scand., 1999, vol. 53, pp. 258-262) in methanol (20 ml), the mixture was stirred at 50° C. for 6 hours. After the reaction mixture was poured into a 1% aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate (three times), the organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by concentrating the organic layer was dissolved in N,N-dimethylformamide (100 ml). After sodium hydride (55% oily, 7.77 g, 178 mmol) was added to the solution under ice-cooling and the mixture was stirred for 30 minutes, chloromethyl methyl ether (13.5 ml, 178 mmol) was added thereto and the mixture was stirred at room temperature for 2 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate (twice), the organic layer was successively washed with 0.5N hydrochloric acid, a 5% aqueous sodium hydrogencarbonate solution, water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=14/1-10/1) to give 1-tert-butyl-3-(dimethoxymethyl)-2-(methoxymethoxy)benzene (10.4 g, yield: 24%).

Provenance & Evidence