Acetic Anhydride → Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl ester

HRID 526152

Reaction equation

HRID 526152 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH:10](OCC)(OCC)[O:11][CH2:12][CH3:13].C(OC(=O)C)(=O)C>>[CH2:12]([O:11][CH:10]=[C:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8868Ethyl AcetoacetateHCID 31214Ethyl orthoformate

Product 1

HCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl esterYield 70%

Conditions

Temperature
135 °C

Procedure

A mixture of ethyl acetoacetate (100 g, 0.77 mol), triethyl orthoformate (130 g, 0.92 mol), and acetic anhydride (150 g, 1.5 mol) was heated at 135° C. for 6-18 h in a round bottomed flask that was equipped with a distillation apparatus to collect the ethanol generated during the reaction. The reaction was cooled, concentrated and the residue was distilled under high vacuum to obtain the desired product (100 g, 70%) as a pale yellow oil: ESI MS m/z 187 [M+H]+.

Workup

  1. customwas equipped with a distillation apparatus
  2. customto collect the ethanol
  3. customgenerated during the reaction
  4. temperatureThe reaction was cooled
  5. concentrationconcentrated
  6. distillationthe residue was distilled under high vacuum

Sources & evidence

ORD record
ord-8570c88f10834a9a95744fb4189550c1
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Linked notes

Loading…