Methanol → 3-Ethylaminophenol

HRID 1382182Notes

Reaction equation

HRID 1382182 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=O)[CH3:2].B.CSC.CO>O1CCCC1.ClCCl>[CH2:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 3

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

Product 1

HCID 5789913-EthylaminophenolYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 161 g of 3-acetamidophenol in 800 ml of tetrahydrofuran was added dropwise over 1-2 hr 275 ml of a 1.0M solution of borane-methyl sulfide in dichloromethane. The reaction was heated to reflux 4-5 hr and then poured slowly into 1 l of methanol. The solvent was evaporated to a heavy syrup which deposited crystals on cooling and scratching. The solid was collected by filtration and redisolved in methanol. Evaporation and crystallization as above gave a 74% yield of 3-(ethylamino) phenol.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux 4-5 hr
  3. customThe solvent was evaporated to a heavy syrup which
  4. temperatureon cooling
  5. filtrationThe solid was collected by filtration
  6. customEvaporation and crystallization as

Sources & evidence

ORD record
ord-fe4ec14797da448ca12941ce7da69e92
Source dataset
uspto-grants-1989_02
Patent number
US04806488

Reaction notes

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