Reaktion #2007788

Reaktionsgleichung

racemic 2-hydroxyoctanoic acid

benzyl bromide

triethylamine

→

benzyl 2-hydroxyoctanoate

Lösungsmittel

ethylacetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent is thereafter evaporated
2. 2
   Waschenthe organic layer is then washed with a saturated solution of NaHCO3 and H2O (2×)
3. 3
   TrocknenThe organic layer is dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated

Vorschrift

To a solution of a commercially available racemic 2-hydroxyoctanoic acid mixture (1.00 g, 6.2 mmol.) in HPLC-grade ethylacetate (30 ml), there are added in succession benzyl bromide (2.22 ml; 18.7 mmol.), triethylamine (2.6 ml, 18.7 mmol.) and tetrabutylammonium iodide (1.15 g; 3.12 mmol.). The solution is stirred for 18 hours at room temperature and the solvent is thereafter evaporated. The residue is taken up into ether and the organic layer is then washed with a saturated solution of NaHCO3 and H2O (2×). The organic layer is dried over MgSO4, filtered and evaporated to yield crude benzyl 2-hydroxyoctanoate (Rf=0.57 in a 3/1 petroleum ether/EtOAc mixture; phosphomolybdinium compound and U.V. color development agent)

Quelle