Sulfuric Acid → 2-Butenoic acid, 3-ethoxy-, ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([CH3:8])=[O:7])[CH3:2].OS(O)(=O)=O.[CH2:15](OC(OCC)OCC)[CH3:16]>C(O)C>[CH2:1]([O:3][C:4](=[O:9])[CH:5]=[C:6]([O:7][CH2:15][CH3:16])[CH3:8])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of ethylacetoacetate (2.7 kg, 20.74 mol) in ethanol (4 L) was added conc.H2SO4 (4 ml) at 25° C. under a nitrogen atmosphere. The mixture was heated to 50° C. before adding triethylorthoformate (3073.6 g, 20.74 mol) drop wise. The mixture was stirred at 50° C. for 16 h. The mixture was concentrated under reduced pressure to give the title compound (2.8 kg, 85%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 4.9 (s, 1H), 4.1 (m, 2H), 3.7 (m, 2H), 2.2 (s, 3H), 1.2 (m, 3H), 1.1 (m, 3H).
Workup
- customat 25° C.
- concentrationThe mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fb0853b2486949ee815bebb6944c9f03
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809363B2
Reaction notes
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