N-bromobutanimide → HCID 12452841, compound
Reaction equation
[C:1]([C:4](=[CH:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH:12]([C:11]1[O:3][C:1]([CH3:2])=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:10]=1)([CH3:13])[CH3:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3.97 g (0.02 mole) ethyl 2-acetyl-5-methyl-2-hexenoate and 3.55 g (0.02 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 2.5 hours. After cooling, the succinimide was removed by filtration and the solution concentrated by rotary evaporation. Distillation of the crude product gave 3.33 g (85% ) of ethyl 5-isopropyl-2-methyl-3-furoate, bp 112°-114° C. (11 mm).
Workup
- temperaturewas heated
- temperatureat reflux for 2.5 hours
- temperatureAfter cooling
- customthe succinimide was removed by filtration
- concentrationthe solution concentrated by rotary evaporation
- distillationDistillation of the crude product
Sources & evidence
- ORD record
- ord-0728c37e81da434bb73d2191524a42e2
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04025537
Reaction notes
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