Methanol → HCID 22723509, compound

Participants

Reaction Steps

To the reaction mixture obtained in Example 2 were added 10% aqueous sodium hydroxide solution (113.8 g) and methanol (20 mL), and the mixture was stirred at room temperature overnight. The disappearance of tert-butyl 4-cyano-3-hydroxy-4-methylpentanoate was confirmed by gas chromatography (GC). Toluene (50 mL) was added and the mixture was stirred and then partitioned to remove the toluene layer. 20% Aqueous hydrochloric acid solution (67.5 g) was added to the aqueous layer to adjust its pH to an acidic one (ca. pH 1-2) and the mixture was extracted twice with ethyl acetate (150 mL). The ethyl acetate layer was concentrated under reduced pressure to give 4-cyano-3-hydroxy-4-methylpentanoic acid (19.9 g) as an oil. When left standing, this oil crystallized. The yield was 89% relative to tert-butyl 4-cyano-3-hydroxy-4-methylpentanoate.

Provenance & Evidence