D-Phenylalanine → (R)-3-phenyllactic acid

Participants

Reaction Conditions

Reaction Steps

Following the procedure of Johnson, 1980, D-phenylalanine (16.5 g, 100 mmol) was dissolved in 1N H2SO4 (150 ml) and cooled to 0° C. A solution of NaNO2 (10.5 g, 150 mmol) in water (50 ml) was added dropwise. The mixture was stirred for 2 h at 0° C. and for 3 h at 25° C. The product was extracted into ether (5×100 ml) and the combined ether extracts were dried over Na2SO4 and concentrated in vacuo to about 100 ml. Hexane (300 ml) was added and the product which crystallized out was collected by vacuum filtration to afford the title compound as a colorless solid (9 g, 54%); mp=124°-125° C.

Provenance & Evidence