Hydrochloric Acid → 3-(4-Methoxyphenoxy)propionic acid

HRID 500435Notes

Reaction equation

HRID 500435 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Cl[CH2:13][CH2:14][C:15]([OH:17])=[O:16].Cl>O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78993-Chloropropionic acidHCID 90154-MethoxyphenolHCID 14797Potassium Hydroxide

Product 1

HCID 2904783-(4-Methoxyphenoxy)propionic acidYield 18.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Solid KOH 6.80 g, (0.122 mol) and H2O (10 ml) are added to para-methoxyphenol 7.0 g (0.0564 mol), the resultant mixture is stirred at the room temperature while 3-chloropropanoic acid (6.12 g, 0.0564 mol) is added to thereof. Then the mixture is stirred and heated to reflux for 3 h. The reaction solution is acidified to pH 2 by adding concentrated aqueous HCl and extracted with ether. The combined ether extracts is then washed with 10% aqueous NaHCO3 and acidified to pH 3-4 by adding concentrated aqueous HCl, and precipitate is formed. The residue is filtered and recrystallized by benzene to provide needle crystal 2.0 g. m.p.: 102-103° C., yield: 18.1%.

Workup

  1. additionis added to thereof
  2. temperatureheated
  3. temperatureto reflux for 3 h
  4. extractionextracted with ether
  5. washThe combined ether extracts is then washed with 10% aqueous NaHCO3
  6. additionby adding concentrated aqueous HCl
  7. customprecipitate is formed
  8. filtrationThe residue is filtered
  9. customrecrystallized by benzene

Sources & evidence

ORD record
ord-15be5c1b66894feba1b723962a91b295
Source dataset
uspto-grants-2010_08
Patent number
US07772230B2

Reaction notes

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