Benzyl Chloride → 3-(Benzoxy)-5-chlorobenzoic acid

HRID 1606753Notes

Reaction equation

HRID 1606753 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH2:14]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([OH:7])=[O:6])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 130716463-Chloro-5-hydroxybenzoic Acid

Product 1

HCID 108799093-(Benzoxy)-5-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 173 mg. (1 m mole) of 3-hydroxy-5-chlorobenzoic acid in 2 ml. of dimethylformamide is added 85 mg. (2 m moles) of 56.6% sodium hydride in an oil suspension. After ten minutes, the resulting suspension is treated with 130 mg. (1 m mole) of benzyl chloride and the mixture heated to 100° C. for one hour. The reaction mixture is then cooled, diluted with 5 ml. of water, and extracted with ether. The aqueous phase is separated, acidified with 6N hydrochloric acid and the product extracted with ether. The ether solvent is removed in vacuo and the residual product triturated with water and filtered. The dried product is sublimed at 125° C. and 0.02 mm of pressure to provide 50 mg. of the desired produce, m.p. 127-129° C.

Workup

  1. waitAfter ten minutes
  2. additionthe resulting suspension is treated with 130 mg
  3. temperatureThe reaction mixture is then cooled
  4. additiondiluted with 5 ml
  5. extractionof water, and extracted with ether
  6. customThe aqueous phase is separated
  7. extractionthe product extracted with ether
  8. customThe ether solvent is removed in vacuo
  9. customthe residual product triturated with water
  10. filtrationfiltered
  11. customis sublimed at 125° C.
  12. custom0.02 mm of pressure to provide 50 mg
  13. customof the desired produce

Sources & evidence

ORD record
ord-e4b5523bd919435fb296b771a82c720e
Source dataset
uspto-grants-1976_04
Patent number
US03953595

Reaction notes

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