Ethanol → 2,4-D-ethyl ester

HRID 1939878Notes

Reaction equation

HRID 1939878 reaction equation
OS(O)(=O)=O.[Cl:6][C:7]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:8]=1[O:9][CH2:10][C:11]([OH:13])=[O:12].[CH2:19](O)[CH3:20]>>[Cl:6][C:7]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:8]=1[O:9][CH2:10][C:11]([O:13][CH2:19][CH3:20])=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1486(2,4-Dichlorophenoxy)Acetic Acid

Product 1

HCID 107802,4-D-ethyl esterYield 53%

Procedure

1.3 g (14 mmol) of H2SO4 were added to 15.0 g (68 mmol) of 2,4-dichlorophenoxyacetic acid in 20 ml of ethanol, and the mixture was refluxed for 5 hours. The mixture was subsequently concentrated in vacuo, the residue was poured into 100 ml of ice-water, the organic phase was separated off, and the aqueous phase was extracted using ether. The combined organic phases were washed using 2N Na2CO3 solution and water, dried over magnesium sulfate and concentrated. 8.9 g (53% of theory) of ethyl 2,4-dichlorophenoxyacetate were obtained as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. concentrationThe mixture was subsequently concentrated in vacuo
  3. additionthe residue was poured into 100 ml of ice-water
  4. customthe organic phase was separated off
  5. extractionthe aqueous phase was extracted
  6. washThe combined organic phases were washed
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-33504bd217a745aa92858c5740299f06
Source dataset
uspto-grants-1997_12
Patent number
US05698539

Reaction notes

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