Phenol → 5-Chloro-2-(phenoxymethyl)benzoic acid

HRID 2083758

Reaction equation

HRID 2083758 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].[Cl:12][C:13]1[CH:22]=[C:21]2[C:16]([CH2:17][O:18][C:19]2=[O:20])=[CH:15][CH:14]=1>CN(C)C=O>[O:9]([CH2:17][C:16]1[CH:15]=[CH:14][C:13]([Cl:12])=[CH:22][C:21]=1[C:19]([OH:20])=[O:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 71741656-Chloro-3H-isobenzofuran-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 203575185-Chloro-2-(phenoxymethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (1.0 mol) is suspended in about 300 ml. of dimethylformamide and phenol (1.0 mol) in about 200 ml. of dimethylformamide is added dropwise, keeping the reaction temperature around 25° C. The mixture is stirred until hydrogen evolution is completed. 6-Chlorophthalide (1.0 mol) in about 250 ml. of dimethylformamide is then added slowly. The resulting mixture is refluxed for 2 hours and allowed to stand at room temperature overnight. The reaction mixture is diluted with ice/water and extracted several times with ether. The aqueous fraction is acidified with dilute hydrochloric acid and extracted with ether. The ether is dried and concentrated to a gummy solid which is recrystallized from a minimum volume of alcohol to give 2-phenoxymethyl-5-chlorobenzoic acid, m.p. 149°-155° C.

Workup

  1. customthe reaction temperature around 25° C
  2. temperatureThe resulting mixture is refluxed for 2 hours
  3. extractionextracted several times with ether
  4. extractionextracted with ether
  5. dry with materialThe ether is dried
  6. concentrationconcentrated to a gummy solid which
  7. customis recrystallized from a minimum volume of alcohol

Sources & evidence

ORD record
ord-542d468f5f9c4325a7f51a97209a6155
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Linked notes

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