Ethanol → 3-Chloro-5-methylphenylethyl acetate

HRID 420552Notes

Reaction equation

HRID 420552 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#N)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH-:12].[Na+].S(=O)(=O)(O)O.[CH2:19]([OH:21])[CH3:20]>>[C:19]([O:12][CH2:10][CH2:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 226001322-(3-Chloro-5-methylphenyl)acetonitrile

Product 1

HCID 666578653-Chloro-5-methylphenylethyl acetate

Conditions

Temperature
80 °C

Procedure

To [(3-chloro-5-methylphenyl)]acetonitrile (0.38 g; 2.29 mmol) were added 2N aqueous sodium hydroxide solution (2.1 ml) and ethanol (5 ml). The mixture was stirred at 80° C. for 1 hour. The reaction solution was concentrated under reduced pressure. To the residue were added water and 2N-aqueous HCl to become neutral. Ethyl acetate was added thereto and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure to give colorless crystal. Concentrated sulfuric acid (0.02 ml) and ethanol (2 ml) were added thereto, and the mixture was refluxed for 5 hours. The reaction solution was concentrated under reduced pressure. To the residue were added water and 2N-aqueous sodium hydroxide solution to become neutral. Ethyl acetate was added thereto and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1) to give 3-chloro-5-methylphenylethyl acetate as colorless oil (0.31 g; 63%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionTo the residue were added water and 2N-aqueous HCl
  3. additionEthyl acetate was added
  4. extractionextracted
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated under reduced pressure
  8. customto give colorless crystal
  9. temperaturethe mixture was refluxed for 5 hours
  10. concentrationThe reaction solution was concentrated under reduced pressure
  11. additionTo the residue were added water and 2N-aqueous sodium hydroxide solution
  12. additionEthyl acetate was added
  13. extractionextracted
  14. washThe organic layer was washed with brine
  15. dry with materialdried over anhydrous sodium sulphate
  16. customevaporated under reduced pressure
  17. customThe residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-ccc1ad67b8c34598a74acbf1031fdd9f
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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