2,4-Di-tert-butylphenol → Methyl (2R)-2-(2,4-Di-t-butylphenyloxy)propanate

Participants

Reaction Steps

Potassium carbonate (5.66 g, 41 mmol) and 2,4-di-t-butylphenol (8.87 g, 43 mmol) were dissolved in dimethyl sulfoxide (175 mL) at 25° C. and allowed to stir overnight under a nitrogen atmosphere to ensure complete anion formation. A solution of 10.0 g (41 mmol) of methyl (2S)-2-(phenylsulfonyl)oxypropanate (12) in dimethyl sulfoxide (50 mL) was added to the anion at 25° C. and the reaction mixture was allowed to stir overnight. The reaction was quenched with water (200 mL) and the phases were separated. The aqueous phase was extracted with perchloroethylene (3×200 mL). The combined organic extracts were washed with water (3×300 mL), a saturated aqueous sodium chloride solution (1×300 mL) and dried (MgSO4). Concentration and purification by flash chromatography on silica gel (EM silica gel 60, 0.040-0.063 partical size, 230-400 Mesh, column size: 7 cm diameter×18 cm length) using hexane and ethyl acetate (29:1) afforded 10.1 g (77%) of methyl (2R)-2-(2,4-di-t-butylphenyloxy)propanate (17) as a thick oil: 1H NMR (CDCl3) δ1.29 (s, 9 H), 1.43 (s, 9 H), 1.60-1.65 (d, 3 H), 3.73 (s, 3 H), 4.75-4.82 (q, 1 H), 6.54-6.57 (d, 1 H), 7.08-7.12 (d, 1 H), 7.33 (s, 1 H); 13C NMR (CDCl3) δ172.9, 153.7, 143.0, 137.2, 124.2, 123.1, 110.5, 71.7, 52.0, 5.0, 34.2, 31.5, 29.9, 18.6; IR (neat) 2962 (vs), 1764 (s), 1740 (s), 1497 (s), 1235 (vs) cm-1.

Provenance & Evidence