Methanol → 3-Ethylaminophenol

HRID 329354Notes

Reaction equation

HRID 329354 reaction equation
B.CSC.[C:5]([NH:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)(=O)[CH3:6].CO>C1COCC1>[CH2:5]([NH:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 121243-HydroxyacetanilideHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 5789913-EthylaminophenolYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.0 M solution of borane-methyl sulfide in dichloromehtane (275 ml) was added dropwise to a solution of 3-acetamidophenol (161 g) in THF (800 ml) over about 1 to 2 hours. The mixture was heated to reflux temperature for about 4 hours and was then poured slowly into methanol (1 liter). The solvent was evaporated to a heavy syrup, which deposited crystals on cooling and scratching. The solid was collected by filtration and redissolved in methanol. Evaporation and recrystallization as above gave a 74% yield of the compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature for about 4 hours
  3. customThe solvent was evaporated to a heavy syrup, which
  4. temperatureon cooling
  5. filtrationThe solid was collected by filtration
  6. dissolutionredissolved in methanol
  7. customEvaporation and recrystallization as

Sources & evidence

ORD record
ord-e28f1d3bd11741938f68267a8c5a5222
Source dataset
uspto-grants-1990_01
Patent number
US04891324

Reaction notes

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