1,2-Dichloroethane → Ethyl 3-hydroxypentanoate

HRID 653603Notes

Reaction equation

HRID 653603 reaction equation
Cl[CH2:2][CH2:3]Cl.[CH2:5]([OH:7])[CH3:6].S(=O)(=O)(O)O.O.[C:14]([O:17][CH2:18][CH3:19])(=[O:16])C>>[OH:7][CH:5]([CH2:2][CH3:3])[CH2:6][C:14]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 8857Ethyl Acetate

Product 1

HCID 316884Ethyl 3-hydroxypentanoate

Procedure

The mixture of 1.9 g of ethyl R-(+)-3-butyryloxypentanate, 16 ml of 1,2-dichloroethane, 16 ml of ethanol and 0.3 ml of sulfuric acid was refluxed for 40 hours, water and ethyl acetate was added and the mixture was stirred. The separated organic layer was washed with a saturated aqueous solution of sodium bicarbonate and then with water, and dried on anhydrous magnesium sulfate. The solvent was distilled away, and 1.0 g crude product was obtained. The crude product was chromatographically purified, and 0.63 g of ethyl R-(-)-3-hydroxypentanate. [α]D24 =-29.7° (C=0.90, CHCl3). As described above, the optical purity of the obtained compound was tested by using Eu(hfc)3 as a shift agent. It was 88% ee. Moreover, the formulation of the above compounds was supported well by their NMR charts.

Workup

  1. temperaturewas refluxed for 40 hours
  2. washThe separated organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materialwith water, and dried on anhydrous magnesium sulfate
  4. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-6e9378de7e4649a7a31fceb082d72975
Source dataset
uspto-grants-1992_07
Patent number
US05128252

Reaction notes

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