Water → 3-(Carboxymethyl)-4-chlorobenzoic acid

HRID 471161Notes

Reaction equation

HRID 471161 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[CH2:13][C:14]#N.[OH2:16]>C(O)C>[C:14]([CH2:13][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[Cl:3])[C:8]([OH:10])=[O:9])([OH:16])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 669641494-Chloro-3-(cyanomethyl)benzoic acid

Product 1

HCID 579893203-(Carboxymethyl)-4-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium hydroxide (1.549 g) in water (15 mL) was added to a suspension of 4-chloro-3-(cyanomethyl)benzoic acid (2.07 g) in ethanol (15 mL) and the resulting solution was heated at reflux for 4 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 washed with brine, dried over anhydrous magnesium sulphate and concentrated in vacuo to afford the subtitled compound as a pale brown solid. Yield 2.06 g.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 4 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. washThe combined extracts were washed with brine
  10. dry with materialdried over anhydrous magnesium sulphate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-305312e53583449eafbb1330dbb08d6c
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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