Phthalide → HCID 10611539, compound

HRID 2083772Notes

Reaction equation

HRID 2083772 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[H][H].[C:13]1([C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][O:15]1)=[O:14]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=1[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 6885PhthalideHCID 79333-ChlorophenolHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 10611539HCID 10611539, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

Sodium hydride (0.1 mol) is suspended in 60 ml. of dry dimethylformamide and 0.1 mol of 3-chlorophenol in about 60 ml. of dimethylformamide is added dropwise maintaining the temperature at 25° C. When hydrogen evolution is completed, 0.1 mol of phthalide in about 60 ml. of dimethylformamide is added slowly at 25° C. The mixture is refluxed for two hours, stirred at room temperature overnight, poured into ice-water and extracted with ether. The aqueous fraction is acidified with concentrated hydrochloric acid and extracted with ether. The combined ether fraction is dried and concentrated to give 2-(3-chlorophenoxymethyl) benzoic acid, m.p. 154°-155° C.

Workup

  1. temperatureThe mixture is refluxed for two hours
  2. extractionextracted with ether
  3. extractionextracted with ether
  4. dry with materialThe combined ether fraction is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b4ec2bc315c24d39b39ccc2365dc15c2
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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