Hydrochloric Acid → HCID 18651688, compound

Participants

Reaction Steps

To a solution of 2.0 g (36 mmol) of potassium hydroxide in water (100 mL) and tetrahydrofuran (100 mL) was added 11.48 g (36 mmol) of methyl (2R)-2-(3,5-di-t-butylphenyloxy)propanate (13). The reaction mixture was allowed to stir overnight at room temperature. The reaction mixture was acidified to pH 2 with concentrated hydrochloric acid and the resulting solution was extracted with diethyl ether (3×200 mL). The combined extracts were washed with an aqueous saturated sodium chloride solution (1×300 mL) and dried (MgSO4). Filtration and concentration resulted in a yellowish sludge. The crude product was purified by precipitation from hexane at -78° C. to afford 8.2 g (75%) of (2R)-2-(3,5-di-t-butylphenyloxy)propanoic acid (14) as an off-white crystalline material: 1H NMR (CDCl3) δ1.29 (s, 18 H), 1.64-1.66 (d, 3 H), 4.56-4.82 (q, 1 H), 6.75 (s, 2 H), 7.06 (s, 1 H); 13C NMR (CDCl3) δ177.7, 156.8, 152.5, 116.2, 109.7, 72.3, 35.0, 31.4, 18.4.

Provenance & Evidence