4,4'-Thiobis(2-tert-butyl-6-methylphenol) → Methyl 2-ethyloxirane-2-carboxylate
Reaction equation
[CH2:1]=[C:2]([CH2:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4].C1C=C(Cl)C=C(C(OO)=[O:17])C=1.S(C1C=C(C)C(O)=C(C(C)(C)C)C=1)C1C=C(C)C(O)=C(C(C)(C)C)C=1>ClCCCl>[CH2:7]([C:2]1([C:3]([O:5][CH3:6])=[O:4])[CH2:1][O:17]1)[CH3:8]Participants
5
Conditions
- Temperature
- 80 °C
Procedure
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, 3H) 1.78 (dq, J=14.6, 7.3 Hz, 1H) 2.10 (dq, J=15.4, 7.6 Hz, 1H) 2.80 (dd, J=5.8, 1.0 Hz, 1H) 3.05 (dd, J=5.8, 1.0 Hz, 1H) 3.77 (d, J=1.5 Hz, 3H).
Workup
- temperatureIt was then cooled down
- filtrationsolid filtered
- washFiltrate washed by Na2SO3, NaHCO3, brine and water until clear
- concentrationIt was then concentrated to a light yellow liquid (7.5 g, 41%)
Sources & evidence
- ORD record
- ord-027b9fe8dfa74309b3c3c88122d36f0a
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026234B2
Reaction notes
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