Tetrahydrofuran → 2'-Hydroxy-4'-methoxyacetanilide

HRID 270057Notes

Reaction equation

HRID 270057 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[OH:12])([O-])=O.[H][H].C1C[O:18][CH2:17][CH2:16]1>[Pd]>[OH:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[NH:1][C:17](=[O:18])[CH3:16]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2196355-Methoxy-2-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 41051392'-Hydroxy-4'-methoxyacetanilideYield 80%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
60 °C

Procedure

2-Nitro-5-methoxyphenol (prepared from 3-methoxyphenol, R. J. Maleski, Synthetic Communications, 1993, 23, 343-348) (48.5 g, 0.287 mol) dissolved in THF (1.5 L) was hydrogenated at ambient temperature over night with 10% palladium on carbon (10 g) until 20.3 L of hydrogen was consumed. After filtration and evaporation the residue was suspended in degased water (1.7 L) and acetic anhydride (42.5 mL) was added with stirring. The mixture was heated to 60° C. for 1 h and then cooled to room temperature. The volatiles were removed in vacuo and the solid was washed thoroughly with water and dried in vacuo to give brick-red crystals (41.7 g, 80%).

Workup

  1. customwas consumed
  2. filtrationAfter filtration and evaporation the residue
  3. additionacetic anhydride (42.5 mL) was added
  4. temperaturecooled to room temperature
  5. customThe volatiles were removed in vacuo
  6. washthe solid was washed thoroughly with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-9dc2eff7eedb4014bf7a9f83c185b290
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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