p-Toluenesulfonic acid → Isobutyl acetoacetate

HRID 2845

Reaction equation

HRID 2845 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

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6560IsobutanolHCID 8868Ethyl Acetoacetate

Product 1

HCID 522677Isobutyl acetoacetate

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

  1. temperatureThe solution was refluxed for 18 h
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in ether
  4. additionThe resulted solution was treated with s.s
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo
  8. 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

Linked notes

Loading…