Water → 2-(2,4-dichlorophenoxy)benzoic acid

HRID 1642238Notes

Reaction equation

HRID 1642238 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#N.[OH-:18].[K+].[OH2:20]>CCO>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]([OH:20])=[O:18]

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 27770202-(2,4-Dichlorophenoxy)benzonitrile

Product 1

HCID 120257772-(2,4-dichlorophenoxy)benzoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

AMR01057 A solution of 2-(2,4-dichlorophenoxy)benzonitrile (AMR01045, 1.39 g, 5.26 mmol) and KOH (1.77 g, 31.58 mmol) in EtOH (10 mL) and H2O (10 mL) was heated at reflux for 20 h. After adding water (20 mL) the solution was washed with DCM (3×10 mL). The aqueous was acidified with HCl 1M and a white solid precipitated. It was filtered, washed with water and dried. Flash chromatography on silica gel using DCM to DCM/MeOH 9:1 gradient as eluent gave 2-(2,4-dichlorophenoxy)benzoic acid (1.1 g, 74%) as a white solid, mp 161-163° C. (Lit. 159-162° C.) Rf: 0.36 (DCM/MeOH 9:1). 1H NMR (300 MHz, CDCl3) δ 6.79 (1H, dd, J=8.3, 0.8 Hz, ArH), 7.00 (1H, d, J=8.7 Hz, ArH), 7.23-7.28 (2H, m, ArH), 7.51 (1H, m, ArH), 7.52 (1H, d, J=7.5 Hz, ArH), 8.17 (1H, dd, J=7.8, 1.7 Hz, ArH), and 10.76 (1H, br s, COOH).

Workup

  1. temperatureat reflux for 20 h
  2. washwas washed with DCM (3×10 mL)
  3. customa white solid precipitated
  4. filtrationIt was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-3435a95c40d947c8acea4affb160603b
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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