Thionyl Chloride → HCID 54368633, compound

HRID 2072830Notes

Reaction equation

HRID 2072830 reaction equation
[CH2:1]([O:3][C@@H:4]([CH3:8])[C:5]([OH:7])=[O:6])[CH3:2].S(Cl)(Cl)=O.[CH3:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(OCC)(=[O:21])C>>[CH2:1]([O:3][C@@H:4]([CH3:8])[C:5]([O:7][C:15]1[CH:14]=[CH:13][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:6])[CH3:2]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 21226206Ethyl acetate hexaneHCID 28197406HCID 28197406, compound

Product 1

HCID 54368633HCID 54368633, compound

Procedure

5.6 g of the resulting (s)-2-ethoxypropionic acid was added to 10 ml of thionyl chloride, and the mixture was refluxed for 5 hours. Thionyl chloride was then evaporated under reduced pressure, and a solution of 9.0 g of hydroquinone in 50 ml of dry pyridine was added, and the mixture was stirred at 30° to 40° C. for 20 hours. The reaction mixture was dissolved in a large amount of ethyl acetate, washed with dilute hydrochloric acid several times and then with water, and dried over anhydrous sodium sulfate. The ethyl acetate solution was concentrated and from the residue, 4.6 g of the desired oily product was obtained by silica gel column chromatography using hexane/ethyl acetate as an eluent.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customThionyl chloride was then evaporated under reduced pressure
  3. additiona solution of 9.0 g of hydroquinone in 50 ml of dry pyridine was added
  4. dissolutionThe reaction mixture was dissolved in a large amount of ethyl acetate
  5. washwashed with dilute hydrochloric acid several times
  6. dry with materialwith water, and dried over anhydrous sodium sulfate
  7. concentrationThe ethyl acetate solution was concentrated and from the residue, 4.6 g of the desired oily product
  8. customwas obtained by silica gel column chromatography

Sources & evidence

ORD record
ord-587dba0fd5e84d4789cf007eca1bcc60
Source dataset
uspto-grants-1990_04
Patent number
US04914224

Reaction notes

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