Ethanol → Ethyl Acetoacetate

HRID 1184950Notes

Reaction equation

HRID 1184950 reaction equation
[CH2:1]([OH:3])[CH3:2].[C:4]([OH:10])(=[O:9])[C:5](C)(C)C.O.[C:12]1(C)C=CC(S(O)(=O)=O)=C[CH:13]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([CH2:5][C:4]([O:10][CH2:12][CH3:13])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 6417Pivalic acidHCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 8868Ethyl AcetoacetateYield 188.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (100 ml), ethanol (19.86 g, 431.16 mmol) and pivalic acid (31.64 g, 359.30 mmol) were added into a 200-ml flask in this order at room temperature and then p-toluenesulfonic acid monohydrate (10.25 g, 53.90 mmol) was charged thereto. The solution was gently heated and subjected to reflux dehydration for 3 to 5 hours. After reflux dehydration, the solution was cooled to around room temperature, added with triethylamine (9.09 g, 89.83 mmol) at room temperature, stirred and then added with silica gel. After stirring for a while, the silica gel was filtered off. After the solvent of the filtrate was removed in vacuum distillation, ethyl acetylacetate (13.2 g, 32%) was isolated in distillation.

Workup

  1. temperatureThe solution was gently heated
  2. temperatureto reflux dehydration for 3 to 5 hours
  3. temperatureAfter reflux dehydration
  4. temperaturethe solution was cooled to around room temperature
  5. additionadded with silica gel
  6. stirringAfter stirring for a while
  7. filtrationthe silica gel was filtered off
  8. customAfter the solvent of the filtrate was removed in vacuum distillation

Sources & evidence

ORD record
ord-39b5208df70e4b33b56d37dcc7a654cb
Source dataset
uspto-grants-2014_03
Patent number
US08669375B2

Reaction notes

Loading…