Benzyl Alcohol → 6-Benzyloxy-2,3,4-trifluorobenzoic acid

HRID 1654488Notes

Reaction equation

HRID 1654488 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[H-].[Na+].[F:12][C:13]1[C:28]([F:29])=[C:27]([F:30])[CH:26]=[C:25](F)[C:14]=1[C:15]([O:17]CC1C=CC=CC=1)=[O:16]>C1C=CC=CC=1.CCCCCC.C(O)(=O)C>[CH2:1]([O:8][C:25]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:12])[C:28]([F:29])=[C:27]([F:30])[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 20077975Benzyl 2,3,4,6-tetrafluorobenzoate

Product 1

HCID 200780176-Benzyloxy-2,3,4-trifluorobenzoic acidYield 31.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

6.5 g of benzyl alcohol was dissolved in 150 ml of benzene. While the resultant solution was cooled with water, 2.4 g of sodium hydride (60%) was added and reacted. To the reaction mixture was added 15 g of benzyl 2,3,4,6-tetrafluorobenzoate, and stirred at room temperature for 1 hour. 3.6 g of acetic acid was added, followed by the removal of the solvent by distillation. To the residue, 6.5 g of potassium hydroxide and 50 ml of water and 100 ml of methanol were added. They were reacted at 50° C. for 30 minutes. 6 g of acetic acid was added, followed by the removal of the solvent by distillation. To the residue were added 50 ml of benzene and 7% aq. potassium hydroxide solution. The resultant mixture was shaken, followed by separation into two layers. Concentrated hydrochloric acid was added to the water layer so that the water layer was rendered acidic. The thus-acidified water layer was extracted twice with 100 ml portions of chloroform. The extract was treated with anhydrous magnesium sulfate and the solvent was distilled out. A solid thus formed was dispersed in n-hexane and then collected by filtration, whereby 4.7 g of 6-benzyloxy-2,3,4-trifluorobenzoic acid was obtained as colorless powder.

Workup

  1. additionwas added
  2. customreacted
  3. customfollowed by the removal of the solvent by distillation
  4. additionTo the residue, 6.5 g of potassium hydroxide and 50 ml of water and 100 ml of methanol were added
  5. customThey were reacted at 50° C. for 30 minutes
  6. customfollowed by the removal of the solvent by distillation
  7. additionTo the residue were added 50 ml of benzene and 7% aq. potassium hydroxide solution
  8. stirringThe resultant mixture was shaken
  9. customfollowed by separation into two layers
  10. additionConcentrated hydrochloric acid was added to the water layer so that the water layer
  11. extractionThe thus-acidified water layer was extracted twice with 100 ml portions of chloroform
  12. additionThe extract was treated with anhydrous magnesium sulfate
  13. distillationthe solvent was distilled out
  14. customA solid thus formed
  15. filtrationcollected by filtration

Sources & evidence

ORD record
ord-75136664e0eb4129bb09e293ed15afc9
Source dataset
uspto-grants-1995_04
Patent number
US05407932

Reaction notes

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