Reaktion #2393311

Reaktionsgleichung

crotonaldehyde

sodium acetate

ethyl chloroacetoacetate

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title product

Ausbeute 65.0%

Ethyl 2-Hydroxy-6-methylbenzoate

Ausbeute 65.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis heated
2. 2
   Temperaturto reflux temperature under N2
3. 3
   Temperaturperiod, heated
4. 4
   Temperaturat reflux temperature for 16 hr
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigeto give a residue
7. 7
   SonstigeThe residue is partitioned between ethyl acetate and water
8. 8
   workup.ADDITIONThe organic phase is diluted with hexanes
9. 9
   Waschenwashed sequentially with water and aqueous NaHCO3
10. 10
    Einengenconcentrated in vacuo

Vorschrift

A stirred mixture of crotonaldehyde (21.0 g, 0.30 mol) and anhydrous sodium acetate (25.0 g, 0.30 mol) in glacial acetic acid is heated to reflux temperature under N2, treated dropwise with ethyl chloroacetoacetate (41.1 g, 95%, 0.25 mol) over a 2.25 hr. period, heated at reflux temperature for 16 hr., cooled to room temperature and concentrated in vacuo to give a residue. The residue is partitioned between ethyl acetate and water. The organic phase is diluted with hexanes, washed sequentially with water and aqueous NaHCO3 and concentrated in vacuo to give the title product as an oil, 41.0 g, 71.4% purity (65% yield), characterized by NMR analysis.

Quelle