Sodium Hydroxide → HCID 20475020, compound

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Reaction Steps

To a chilled solution of 10.14 g of the mixture containing octyl 3-acetoxyphenylacetamide and 100 ml of methanol was added 12.63 ml of 5 N NaOH. The mixture was stirred at room temperature for 3 hours after which the methanol was removed in vacuuo. The residue was dissolved in 100 ml of 1 N NaOH and extracted with 50 ml of ether. The resulting aqueous phase was acidified with conc. hydrochloric acid and extracted twice with 100 ml of ether. The combined ether extracts were washed with 75 ml of water and 75 ml of brine, dried (MgSO4), filtered, and evaporated to provide 7.55 g of crude product which was recrystallized from toluene-pentane to yield 5.03 g of octyl 3-hydroxyphenylacetamide, m.p. 60°-62° C. Anal. Calc'd for C16H25NO2 : C, 73.00; H, 9.58; N, 5.32. Found: C, 72.86; H, 9.63; N, 5.16.

Provenance & Evidence