Acetic Anhydride → Ethyl 2-butyryl-3-ethoxyacrylate

HRID 1382352Notes

Reaction equation

HRID 1382352 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH:12](OCC)(OCC)[O:13][CH2:14][CH3:15].C(OC(=O)C)(=O)C>>[C:1]([C:6](=[CH:12][O:13][CH2:14][CH3:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 3359484Ethyl 2-butyryl-3-ethoxyacrylate

Procedure

A mixture of ethyl butyrylacetate (100 g, 0.63 mol), triethyl orthoformate (210 ml, 1.26 mol) and acetic anhydride (60 ml, 0.63 mol) was heated under reflux for 6 hours, then excess triethyl orthoformate evaporated in vacuo. The residue consisted mainly of ethyl 2-butyryl-3-ethoxyacrylate as a mixture of E and Z isomers, and was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customexcess triethyl orthoformate evaporated in vacuo
  4. additionThe residue consisted mainly of ethyl 2-butyryl-3-ethoxyacrylate as a mixture of E and Z isomers
  5. customwas used without further purification

Sources & evidence

ORD record
ord-5b3715e322834a3f8d0b03499a6624b3
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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