Hydrochloric Acid → HCID 13895882, compound

Participants

Reaction Steps

A portion (3.4 g, 0.013 mol) of the methyl 2-nitro-4,5-dimethoxyphenylacetate produced in (2) above and sodium borohydride (2.52 g, 0.067 mol) were dissolved in tetrahydrofuran (100 ml), followed by heating at the reflux temperature for 30 min. Methanol (10 ml) was added dropwise to the reaction mixture over 30 min, followed by heating for 1 h. The mixture was cooled to room temperature and the residual reagents were decomposed with an aqueous solution of 1N HCl, followed by neutralization with an aqueous solution of sodium bicarbonate and three extractions with ethyl acetate. The organic extracts were dried with sodium sulfate and the solvent was evaporated, with the residue being purified by being subjected to column chromatography on silica gel using, as an eluent, ethyl acetate containing n-hexane (33%). The fractions containing the end product were collected and the solvent was evaporated to yield the end compound 2-nitro-4,5-dimethoxyphenethyl alcohol (3.0 g) as a pale yellow solid mass.

Provenance & Evidence