Guaiacol → HCID 11065034, compound

HRID 1636078Notes

Reaction equation

HRID 1636078 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].[C:10]1([CH3:20])[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17](O)=[O:18].O=P(Cl)(Cl)Cl>[Cl-].[Cl-].[Zn+2]>[OH:3][C:2]1[CH:4]=[CH:5][C:6]([C:17](=[O:18])[CH2:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH3:20])=[CH:7][C:1]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 24813Phosphorus oxychlorideHCID 69519o-Tolylacetic acid

Product 1

HCID 11065034HCID 11065034, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
80 °C

Procedure

To a mixture of guaiacol (1.24 g, 10 mmol), o-tolylacetic acid (1.50 9, 10 mmol), and ZnCl2 (5 g, 36.7 mmol) there was added POCl3 (15 mL, 161 mmol) and the resulting suspension was stirred and heated to 80° C. for 1.5 h. The reaction mixture was cooled and poured onto ice/water and the resulting suspension was stirred at room temperature for 1 h and then extracted with ethyl acetate. The organic layer was separated, washed with brine and dried with sodium sulphate. Volatiles were evaporated under reduced pressure and the residue was dissolved in diethylether. The solution was extracted twice with 50 mL of 2N aqueous solution of NaOH and the combined aqueous layers were combined and acidified with hydrochloric acid to pH=2. The emulsion formed was extracted by ethyl acetate, and the organic layer was washed with brine, dried, and the solvent was evaporated under diminished pressure. The residue was chromatographed on a column of silica gel with a mixture of petroleum ether and ethyl acetate to give 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methylphenyl)-1-ethanone as off white crystals, m.p. 79 to 81° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto ice/water
  3. stirringthe resulting suspension was stirred at room temperature for 1 h
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried with sodium sulphate
  8. customVolatiles were evaporated under reduced pressure
  9. dissolutionthe residue was dissolved in diethylether
  10. extractionThe solution was extracted twice with 50 mL of 2N aqueous solution of NaOH
  11. customThe emulsion formed
  12. extractionwas extracted by ethyl acetate
  13. washthe organic layer was washed with brine
  14. customdried
  15. customthe solvent was evaporated under diminished pressure
  16. customThe residue was chromatographed on a column of silica gel with a mixture of petroleum ether and ethyl acetate

Sources & evidence

ORD record
ord-0f70850d025a49d0812b16efe2474843
Source dataset
uspto-grants-2003_01
Patent number
US06512136B1

Reaction notes

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