Potassium Hydroxide → 4-(2-Chloroethoxy)benzoic acid

HRID 354067Notes

Reaction equation

HRID 354067 reaction equation
C[C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][Cl:14])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[K+]>CO>[Cl:14][CH2:13][CH2:12][O:11][C:9]1[CH:10]=[CH:2][C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23512918methyl 4-(2-Chloroethoxy)-benzoic acid

Product 1

HCID 123892684-(2-Chloroethoxy)benzoic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 4-(2-Chloroethoxy)-benzoic acid (11.8 gm, 53.5 mmol) dissolved in 118 mL of methanol was added 2N KOH (35mL, 1.3 equiv.) and the resulting solution was heated at 50° C. for 24 hrs. The reaction was cooled to room temperature and the methanol evaporated off. The residue was diluted with water and extracted once with ethyl acetate. The aqueous layer was then acidified with 6N HCl and a precipitate formed which was filtered off, washed well with water, and pumped dry under vacuum to yield 10 gm of the title compound.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe methanol evaporated off
  3. additionThe residue was diluted with water
  4. extractionextracted once with ethyl acetate
  5. customa precipitate formed which
  6. filtrationwas filtered off
  7. washwashed well with water
  8. custompumped dry under vacuum

Sources & evidence

ORD record
ord-d7372df631b542349a22e590570c18c4
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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