Dimethylformamide → 4-(Dimethylamino)phenol

HRID 441209Notes

Reaction equation

HRID 441209 reaction equation
S([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[CH:8][CH:7]=1)(O)(=O)=O.[C:14](=O)([O-])[O-].[K+].[K+].IC.CN(C)C=O>O1CCCC1>[CH3:14][N:12]([CH3:13])[C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10198132p-(N-methylamino)phenol sulfate

Product 1

HCID 221744-(Dimethylamino)phenolYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methylaminophenol sulfate (1.00 g) and potassium carbonate (0.88 g) in dry tetrahydrofuran (29 mL) was stirred for 45 minutes at room temperature before iodomethane (0.36 mL) was added. After the reaction was stirred for 18 h, TLC showed incomplete reaction. Dimethylformamide (5 mL) was added to make the reaction mixture homogeneous and stirring was continued. After a total of 42 h, the reaction was evaporated and the residue was suspended in ethyl acetate (75 mL). The suspension was washed (saturated sodium bicarbonate, brine), dried, evaporated and dried under vacuum to give the crude product as an oil. The oil was preadsorbed onto silica gel; and chromatography, eluting with hexane:ethyl acetate (2:1), gave 4-dimethylaminophenol as a white solid (0.26 g); TLC: Rf =0.35, hexane:ethyl acetate (2:1); MS: m/z=138(M+1).

Workup

  1. additionwas added
  2. customreaction
  3. stirringstirring
  4. customAfter a total of 42 h, the reaction was evaporated
  5. washThe suspension was washed (saturated sodium bicarbonate, brine)
  6. customdried
  7. customevaporated
  8. customdried under vacuum
  9. customto give the crude product as an oil
  10. washand chromatography, eluting with hexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-ea96e5ffc30e4a6892e4040ba801b7f6
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

Loading…