Methane, dichloromethoxy- → HCID 19767558, compound

Participants

Reaction Steps

To a 0° solution of 2-t-butyl-1-naphthol (7.6 g, 0.038 mole) in 50 ml of dry dichloromethane was added anhydrous stannic chloride (19.77 g, 0.076 mole). The resulting reaction mixture was stirred at 0° during the dropwise addition of 1,1-dichloromethyl methyl ether (7.75 g, 0.068 mole). The mixture was stirred for 10 minutes at 0° then poured into ice/water. The resulting mixture was extracted with diethyl ether (3×200 ml). The ethereal extracts were washed with water until the aqueous washes had a neutral pH and then dried over magnesium sulphate. The solvent was removed in vacuo to give a solid residue which was triturated with a mixture of diethyl ether: n-pentane (1:4) to give 3.8 g (44% yield) of a crystalline solid, m.p. 195°-196°.

Provenance & Evidence