Hydroxyphenylacetic acid → HCID 19766485, compound

HRID 1591073Notes

Reaction equation

HRID 1591073 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH2:12](Br)[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O.C([N:24](CC)CC)C>ClCCl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[O:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:24]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 6259Phenacyl bromideHCID 8471Triethylamine

Product 1

HCID 19766485HCID 19766485, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 ml of dichloromethane, were dissolved 6.09 g of 4-hydroxyphenyl acetic acid and 7.96 g of phenacyl bromide were dissolved, to which 5.6 ml of triethylamine was added and stirred at room temperature for 2 days. After washing the reaction solution with a 10% hydrochloric acid, it was further washed with an aqueous saturated solution of sodium hydrogen carbonate. After distilling off the dichloromethane under a reduced pressure from the solution, the residue was dissolved in 80 ml of acetic acid and refluxed for three hours with addition of 12.3 g of ammonium acetate. The acetic acid was distilled off under a reduced pressure from the solution. The residue was dissolved in dichloromethane, washed with a 10% hydrochloric acid and an aqueous saturated solution of sodium hydrogen carbonate, and then, the dichloromethane layer was collected. After drying the liquid extract over magnesium sulfate, it was concentrated under a reduced pressure, adsorbed on silica gel column, eluted with chloroform and then crystallized from isopropyl ether to obtain 3.65 g of 2-(4-hydroxybenzyl)-4-phenyloxazole having the melting point of 122° to 124° C.

Workup

  1. additionwas added
  2. washAfter washing the reaction solution with a 10% hydrochloric acid, it
  3. washwas further washed with an aqueous saturated solution of sodium hydrogen carbonate
  4. distillationAfter distilling off the dichloromethane under a reduced pressure from the solution
  5. dissolutionthe residue was dissolved in 80 ml of acetic acid
  6. temperaturerefluxed for three hours with addition of 12.3 g of ammonium acetate
  7. distillationThe acetic acid was distilled off under a reduced pressure from the solution
  8. dissolutionThe residue was dissolved in dichloromethane
  9. washwashed with a 10% hydrochloric acid
  10. customan aqueous saturated solution of sodium hydrogen carbonate, and then, the dichloromethane layer was collected
  11. customAfter drying the liquid
  12. extractionextract over magnesium sulfate, it
  13. concentrationwas concentrated under a reduced pressure
  14. washeluted with chloroform
  15. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-a0f2274603d545b189be992fd6b58a2e
Source dataset
uspto-grants-1993_04
Patent number
US05206255

Reaction notes

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