Water → 5-(Carboxymethyl)-2-chlorobenzoic acid

HRID 1689356Notes

Reaction equation

HRID 1689356 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#N)=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].[OH2:16]>C(O)C>[C:14]([CH2:13][C:10]1[CH:11]=[CH:12][C:4]([Cl:3])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7])([OH:16])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 581685272-Chloro-5-(cyanomethyl)benzoic acid

Product 1

HCID 579893705-(Carboxymethyl)-2-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium hydroxide (0.969 g) in water (10 mL) was added to a solution of 2-chloro-5-(cyanomethyl)benzoic acid (1.25 g) in ethanol (10 mL) and the resulting mixture was heated at reflux for 2.25 hours, then allowed to cool. The mixture was concentrated in vacuo to remove the ethanol and then diluted with water and washed twice with ethyl acetate. The organic phases were discarded, whilst the aqueous phase was acidified to pH 1 with concentrated hydrochloric acid and extracted twice with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulphate and concentrated in vacuo to afford the subtitled compound as a brown gum. Yield 1.38 g.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2.25 hours
  3. temperatureto cool
  4. concentrationThe mixture was concentrated in vacuo
  5. customto remove the ethanol
  6. additiondiluted with water
  7. washwashed twice with ethyl acetate
  8. extractionextracted twice with ethyl acetate
  9. dry with materialThe combined extracts were dried over anhydrous magnesium sulphate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18fc3b1da1f340ad8fda92f166f1ef6f
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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