2-Bromoethanol → HCID 18316809, compound

HRID 276089Notes

Reaction equation

HRID 276089 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:14][CH2:15][OH:16].C([O-])(O)=O.[Na+]>CO>[CH2:1]([N:5]([C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1)[CH2:14][CH2:15][OH:16])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 516892Sodium BicarbonateHCID 111266263-(n-butylamino)phenol

Product 1

HCID 18316809HCID 18316809, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.1 mol of 3-(n-butyl-amino)phenol in 100 ml of methanol is refluxed for 10 h with 0.11 mol of 2-bromoethanol and 0.1 mol of NaHCO3. After cooling, the mixture is filtered, the solvent is removed in vacuo and the residue is fractionated, to give 3-[N-(n-butyl)-N-(2-hydroxyethyl)amino]-phenol in a yield of 54%; b.p. 130-140° C. (5·10−5 torr), m.p. 45-47° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-6908d5c8a2bd4bc7927c3d477e5ecdc0
Source dataset
uspto-grants-2002_03
Patent number
US06353059B2

Reaction notes

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