Guaiacol → HCID 17964393, compound

HRID 1182032Notes

Reaction equation

HRID 1182032 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][C:16](F)=[CH:15][CH:14]=1)=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:9][O:8][C:1]1[CH:7]=[CH:6][CH:5]=[CH:4][C:2]=1[O:3][C:16]1[CH:17]=[CH:18][C:13]([C:11](=[O:12])[CH3:10])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 460GuaiacolHCID 962WaterHCID 98284'-FluoroacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 17964393HCID 17964393, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.15 ml of guaiacol 67, 167 mg of 4-fluoroacetophenone 68 and 335 mg of potassium carbonate are heated in 5 ml of dimethyl sulfoxide at 170° C. in a microwave for 10 min. The reaction solution is poured into water, and the emulsion is extracted three times with an ethyl tert-butyl ether. The combined organic phase is extracted twice with 1 N NaOH and once with saturated NaCl solution, dried and concentrated in vacuo. 240 mg of the desired product are obtained. C15H14O3 (242.28) MS (ESI): 215.10 (M+H+).

Workup

  1. extractionthe emulsion is extracted three times with an ethyl tert-butyl ether
  2. extractionThe combined organic phase is extracted twice with 1 N NaOH and once with saturated NaCl solution
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-398f4820aef94bd68dfc965ac1425b23
Source dataset
uspto-grants-2007_10
Patent number
US07288528B2

Reaction notes

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