Isopropanol → HCID 178440805, compound

Participants

Reaction Conditions

Reaction Steps

Benzylmercaptan (415 ml; 3.5 mol) was added to isopropanol (800 ml), and under cooling, 5.3 N aqueous sodium hydroxide (1000 ml) and an isopropanol solution (800 ml) containing bromoisobutyric acid (1) (296 g; 1.77 mol) were dropwise added thereto. The resulting mixture was heated at 80° C. for 44 hours while stirring. The reaction mixture was combined with water (1000 ml) and washed with ether three times. The aqueous layer was adjusted to pH 2 with 4N hydrochloric acid, followed by extraction with ethyl acetate two times. The ethyl acetate layer was washed with water and a saturated aqueous solution of sodium chloride in order three times. The organic layers were combined together, dried over anhydrous sodium sulfate and concentrated. Ether (5 liters) was added to the residue, and dicyclohexylamine (353 ml) was dropwise added thereto under cooling. Precipitated crystals were collected by filtration and recrystallized from a mixture of methanol and ether to give benzylthioisobutyric acid (dicyclohexylamine salt) (2) (348.7 g; yield, 50%).

Provenance & Evidence