Toluene → HCID 22164641, compound

Participants

Reaction Steps

A solution of 17.25 g (0.43 mol) of 60% sodium hydride in 500 ml of xylene was heated to 100° C. To this was dropwise added over 2 hours a mixture of 69 g (0.39 mol) of 1,1-dimethyl-3-hydroxymethylindane (IX) and 250 ml of toluene. After stirring for 5 hours, 27.1 g (0.215 mol) of dimethyl sulfate was added dropwise to the reaction mixture over 2 hours. After the addition, the mixture was stirred for 3 hours to complete the reaction. 250 ml of water was added to the resulting reaction mixture to separate the water and organic layers. The organic layer was washed with water, an aqueous solution of sodium sulfate, and saturated brine, and dried over anhydrous magnesium sulfate. After removing the solvent, the residue was distilled under reduced pressure to produce 68.3 g (0.36 mol) of 1,1-dimethyl-3-methoxymethylindane at a yield of 92%. The product was a colorless, transparent liquid having a green, herbal, woody odor.

Provenance & Evidence