2-(Dimethoxymethyl)naphthalene

Abstract

[77196-31-7] C13H14O2 (MW 202.25) InChI = 1S/C13H14O2/c1-14-13(15-2)12-8-7-10-5-3-4-6-11(10)9-12/h3-9,13H,1-2H3 InChIKey = DUWXVMIEMVFNGD-UHFFFAOYSA-N (reagent used for the protection of diols as the versatile 2-naphthylmethylene acetal) Alternate Name: 2-naphthaldehyde dimethylacetal. Physical Data: bp 141–143 °C/2 mm Hg; d 1.10 g cm−3. Solubility: soluble in alcohol, ether, and most organic solvents. Form Supplied in: colorless clear liquid. The title reagent is not commercially available, it can be prepared from 2-naphthaldehyde which is commercially available. Preparative Methods: trimethyl orthoformate and Amberlite IR 120 (H+) resin were added to a solution of 2-naphthaldehyde in methanol and stirred overnight at room temperature. The mixture was filtered, neutralized with aq NaHCO3, and evaporated. The residue was dissolved in dichloromethane, washed with water, dried over MgSO4, and evaporated in vacuum. The residue is a yellowish clear liquid, pure enough for synthesis (> 95%). Vacuum distillation can be applied for further purification which gives a colorless liquid. A preparative method without solvent has also been described.1 Handling, Storage, and Precautions: should be kept in a cool and dry place.