Water → 3-(Carboxymethyl)-2-chlorobenzoic acid

HRID 1689413Notes

Reaction equation

HRID 1689413 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[C:12]([CH2:13][C:14]#N)=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].[OH2:16]>C(O)C>[C:14]([CH2:13][C:12]1[C:4]([Cl:3])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])([OH:16])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 579893812-Chloro-3-(cyanomethyl)benzoic acid

Product 1

HCID 579889673-(Carboxymethyl)-2-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium hydroxide (2.976 g) in water (30 mL) was added to a suspension of 2-chloro-3-(cyanomethyl)benzoic acid (example 80, step a) (4.12 g) in ethanol (30 mL) and the resulting solution was heated at reflux for 2 hours, then allowed to cool overnight. 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 three times with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulphate and concentrated in vacuo to afford the crude subtitled compound as a yellow solid. Yield 4.11 g. Used directly.

Workup

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

Sources & evidence

ORD record
ord-266f45c09231452b80e4de0c57b85fd9
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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