Sodium Hydroxide → HCID 19690917, compound

Participants

Reaction Steps

The 29 g. of residual oil described in Example 3 above (ethyl ester of rac. 4-(2-acetamidopropyl)phenoxyacetic acid was refluxed with 16.4 g. of sodium hydroxide (0.41 moles) in 150 ml. of water for 15 hrs., after which the solution was cooled, a trace of flocculent matter removed by filtration and the clear filtrate passed over a column of 750 ml. (0.75 eq) of Dowex® 2-X4 in the hydrogen form. After washing the column with water until the effluent pH was 4-5, the amino acid was eluted with 2 l. of 10% aqueous pyridine. Distillation of the pyridine effluent in a rotary evaporator left a residue of 18 g., m.p. 301°-303° dec.

Provenance & Evidence