4-Formyl-4-methylvaleronitrile → 5-Hydroxy-4,4-dimethylvaleronitrile

Participants

Reaction Steps

To a solution of 47 g (0.376 mmol) of 4,4-dimethyl-5-oxovaleronitrile in 350 mL of methanol, cooled to 0° C. (ice bath), was added, with vigorous stirring and over 15-20 min., 7.9 g (0.209 mmol; 2.22 hydride equiv.) of NaBH4. After the addition was completed, the solution was stirred an additional 30 min. at 0° C. before removing the solvent in vacuo (aspirator). To the residue was added CH2Cl2 followed by careful addition of H2O, and finally 1.2N HCl until pH=1-2 was obtained. The layers were separated and the aqueous one extracted twice (CH2Cl2), saturated with NaCl and extracted again three times with CH2Cl2. After drying the combined organic layers over Na2SO4 and removing the solvent under vacuum (aspirator) 47.7 g (95%) of the title compound, sufficiently pure for the next step, was obtained as a faint yellow oil. TLC: (Silica) Rf =0.26 (ethyl acetate dichloromethane 1:9), detection with molybdophosphoric acid (yellow spot on blue-green).

Provenance & Evidence