Acetic Acid → 2,2'-[(2-methoxyphenyl)imino]diethanol

HRID 344718Notes

Reaction equation

HRID 344718 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:10]1[O:12][CH2:11]1.[C:13](O)(=[O:15])[CH3:14]>O>[OH:15][CH2:13][CH2:14][N:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH2:11][CH2:10][OH:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6354Ethylene OxideHCID 70002-Methoxyaniline

Product 1

HCID 2416342,2'-[(2-methoxyphenyl)imino]diethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.38 g (59.9 mmols) of o-anisidine, 10 ml (202.3 mmols) of ethylene oxide and 150 ml of a solvent mixture of acetic acid and water (9/1) was stirred at room temperature for 40 hours. The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol =30/1) to afford o-[N,N-bis(hydroxyethyl)amino]anisole.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol =30/1)

Sources & evidence

ORD record
ord-9644276bbd8e4e069a7a9e8ba80df488
Source dataset
uspto-grants-1991_10
Patent number
US05053408

Reaction notes

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