Ethanol → alpha-Naphthaleneacetic acid, ethyl ester

HRID 1613331

Reaction equation

HRID 1613331 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH2:19](O)[CH3:20]>>[C:1]1([CH2:11][C:12]([O:14][CH2:19][CH3:20])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 68621-Naphthaleneacetic AcidHCID 24386Thionyl Chloride

Product 1

HCID 62428alpha-Naphthaleneacetic acid, ethyl ester

Procedure

100 g (537 mmol) of naphthalene-1-acetic acid in 200 ml of absolute ethanol are heated to 60° C., while stirring, and 80 ml of thionyl chloride are added slowly in such a way that reflux occurs. Reflux is maintained for 6 h, and the solvent is then evaporated under reduced pressure. The residue is taken up with 200 ml of dichloromethane, the solution is washed with a saturated solution of sodium hydrogen carbonate and then with water, dried over magnesium sulphate and filtered, and the solvent is evaporated under reduced pressure. 104 g (485 mmol) of product are obtained in the form of an oil. n25D =1.5800.

Workup

  1. temperaturethat reflux
  2. temperatureReflux
  3. temperatureis maintained for 6 h
  4. customthe solvent is then evaporated under reduced pressure
  5. washthe solution is washed with a saturated solution of sodium hydrogen carbonate
  6. dry with materialwith water, dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-75d7f7d60033494bb86b7f8e9e79374a
Source dataset
uspto-grants-1993_03
Patent number
US05192797

Linked notes

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