4-Methoxyphenol → 1-(4-(4-Methoxyphenoxy)phenyl)ethan-1-one

HRID 1406341Notes

Reaction equation

HRID 1406341 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)=[O:3].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:7]2[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 98284'-FluoroacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 27772531-(4-(4-Methoxyphenoxy)phenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

138 mg (1 mmol) of 4-fluoroacetophenone were taken and 124 mg (1 mmol) of 4-methoxyphenol were dissolved in DMSO and added thereto, then 200 mg (1.45 mmol) of K2CO3 were added and the mixture was stirred for 8 h at 80° C., then for 6 h at 100° C., then for 3 h at 120° C. and for 3 h at 140° C. The reaction mixture was filtered through basic Alox, washed with DMF/methanol=9/1 and concentrated by rotary evaporation. The substance was purified by reversed-phase chromatography.

Workup

  1. additionadded
  2. waitfor 6 h at 100° C.
  3. waitfor 3 h at 120° C.
  4. waitfor 3 h at 140° C
  5. filtrationThe reaction mixture was filtered through basic Alox
  6. washwashed with DMF/methanol=9/1
  7. concentrationconcentrated by rotary evaporation
  8. customThe substance was purified by reversed-phase chromatography

Sources & evidence

ORD record
ord-6b59cdef5cd747a1abc8d697f91a7ac9
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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