4,4'-Thiobis(2-tert-butyl-6-methylphenol) → Methyl 2-ethyloxirane-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-methylenebutanoate (140 mmol), mCPBA (77%, 67 g, 300 mmol) and 4,4′-thiobis(2-tert-butyl-6-methylphenol) (250 mg, 0.7 mmol) in 100 ml of dry 1,2-dichloroethane was refluxed at 80° C. for 2 d. It was then cooled down, solid filtered. Filtrate washed by Na2SO3, NaHCO3, brine and water until clear. It was then concentrated to a light yellow liquid (7.5 g, 41%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.02 (td, J=7.4, 1.3 Hz, 3 H) 1.78 (dq, J=14.6, 7.3 Hz, 1 H) 2.10 (dq, J=15.4, 7.6 Hz, 1 H) 2.80 (dd, J=5.8, 1.0 Hz, 1 H) 3.05 (dd, J=5.8, 1.0 Hz, 1 H) 3.77 (d, J=1.5 Hz, 3 H).

Provenance & Evidence