Acetic Acid → HCID 23160726, compound

HRID 2246757Notes

Reaction equation

HRID 2246757 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[Cl-].CS(O[CH2:21][CH2:22][NH+:23]([CH3:25])[CH3:24])(=O)=O.C(O)(=O)C>COCCOC>[CH3:24][N:23]([CH3:25])[CH2:22][CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8434EthylparabenHCID 14798Sodium HydroxideHCID 23160713HCID 23160713, compound

Product 1

HCID 23160726HCID 23160726, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

20 g (0.12 mol) of ethyl 4-hydroxybenzoate were dissolved in 300 mL of ethylene glycol dimethyl ether in a nitrogen atmosphere. 11.6 g (0.29 mol) of 60% sodium hydroxide were added in portions over the course of 25 minutes while stirring at room temperature followed by heating to 50° C. and stirring for 1 hour. Moreover, 29.4 g (0.14 mol) of [2-(methanesulfonyloxy)ethyl]dimethylammonium chloride were added in portions over the course of 1 hour at the same temperature followed by additionally stirring for 2 hours. After adding 4 mL of acetic acid while cooling with ice, the precipitate that formed was filtered out. The filtrate was concentrated and ethyl acetate was added to the residue followed by extraction with 3% sulfuric acid. After washing the aqueous phase with ethyl acetate, potassium hydrogen carbonate was added to bring to pH8 followed by extraction with ethyl acetate. The organic layer was dried with magnesium sulfate followed by distilling off the solvent to obtain 26.3 g of the target substance (yield: 92%).

Workup

  1. temperatureby heating to 50° C.
  2. stirringstirring for 1 hour
  3. stirringby additionally stirring for 2 hours
  4. temperaturewhile cooling with ice
  5. customthe precipitate that formed
  6. filtrationwas filtered out
  7. concentrationThe filtrate was concentrated
  8. additionethyl acetate was added to the residue
  9. extractionfollowed by extraction with 3% sulfuric acid
  10. washAfter washing the aqueous phase with ethyl acetate, potassium hydrogen carbonate
  11. additionwas added
  12. extractionfollowed by extraction with ethyl acetate
  13. dry with materialThe organic layer was dried with magnesium sulfate
  14. distillationby distilling off the solvent
  15. customto obtain 26.3 g of the target substance (yield: 92%)

Sources & evidence

ORD record
ord-a9feaa57d316472f886059b660a4595f
Source dataset
uspto-grants-2010_03
Patent number
US07687546B2

Reaction notes

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