2,2-Dimethoxypropane → HCID 21993607, compound

Participants

Reaction Steps

To a suspension of 25.1 g (661 mM) of lithium aluminum hydride in 1300 ml of tetrahydrofuran was added 50.77 g (264.2 mM) of 1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylic acid (trimellitic anhydride) in small portions under ice-cooling and the mixture was stirred at room temperature for one day. To this reaction mixture was added ethyl acetate with ice-cooling to decompose the excess lithium aluminum hydride and water was added until a white precipitate had formed. The precipitate was filtered off with the aid of celite and the celite was washed with ethyl acetate and ethanol. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure. The crude [2,4-bis(hydroxymethyl)-phenyl]methanol thus obtained was dissolved in 100 ml of N,N-dimethylformamide. Then, 100 ml of acetone, 70 ml of 2,2-dimethoxypropane, and 5 g of DL-10-camphorsulfonic acid were added and the mixture was stirred at room temperature overnight. This reaction mixture was diluted with aqueous solution of sodium hydroxide and extracted with 6 portions of ethyl acetate. The pooled organic solution was dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to provide the title compound.

Provenance & Evidence