p-Toluenesulfonic acid → Isobutyl acetoacetate
Reaction equation
[C:1](OCC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:21]([OH:25])[CH:22]([CH3:24])[CH3:23]>>[C:1]([O:25][CH2:21][CH:22]([CH3:24])[CH3:23])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]Participants
4
Procedure
30 ml of ethyl acetoacetate were dissolved in 350 ml of i-butyl alcohol and a catalytic amount of p-toluensulphonic acid (PTSA) was added. The solution was refluxed for 18 h. The reaction mixture was evaporated in vacuo and the residue was dissolved in ether. The resulted solution was treated with s.s. NaHCO3. The organic layer was separated, dried over Na2SO4 and evaporated in vacuo. The crude oil was distilled at 66°-68° C./4 mmHg, to give 18.8 g of the title compound.
Workup
- temperatureThe solution was refluxed for 18 h
- customThe reaction mixture was evaporated in vacuo
- dissolutionthe residue was dissolved in ether
- additionThe resulted solution was treated with s.s
- customThe organic layer was separated
- dry with materialdried over Na2SO4
- customevaporated in vacuo
- distillationThe crude oil was distilled at 66°-68° C./4 mmHg
Sources & evidence
- ORD record
- ord-78feaec48f454c398ecf0ddf11da5e02
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05731322
Reaction notes
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