Hydrochloric Acid → HCID 59377969, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5-amino-2-chloro-4-methyl-phenyl)-acetic acid ethyl ester (0.25 g, 1.09 mmol) in THF (15 ml) was added lithium borohydride (0.059 g, 2.74 mmol) and the mixture was heated at reflux for three hours. The mixture was cooled to 0° C. and acidified to pH 1 with aqueous 2N HCl. The mixture was taken to pH7 by addition of aqueous 2N NaOH and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine dried, over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 1:1) gave 0.203 g (99%) of 2-(5-amino-2-chloro-4-methyl-phenyl)-ethanol as a white solid.

Provenance & Evidence