Acetic Acid → Ethanol, 2,2'-[[4-(phenylmethoxy)phenyl]imino]bis-

HRID 895829Notes

Reaction equation

HRID 895829 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:24]1[O:26][CH2:25]1.[C:27](O)(=[O:29])[CH3:28]>>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([N:14]([CH2:25][CH2:24][OH:26])[CH2:28][CH2:27][OH:29])=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6354Ethylene OxideHCID 8471TriethylamineHCID 27238314-Benzyloxyaniline hydrochloride

Product 1

HCID 254979Ethanol, 2,2'-[[4-(phenylmethoxy)phenyl]imino]bis-Yield 84%

Procedure

4-Benzyloxyaniline hydrochloride 1A (9.32 g, 39.5 mmol) was dissolved in acetic acid (400 mL), triethylamine (6 mL, 43 mmol) was added followed by ethylene oxide (20 mL). The reaction mixture was stirred at room temperature for 72 h, the solvent was evaporated in a rotary evaporator under water pump then under oil pump at 50° C. for 1 h. The residue was then diluted with water (500 mL) and the precipitate recovered by filtration, washed with more water, then dried in dessicator over P2O5 to afford 2A (9.6 g, 84%) as a pale brown powder.

Workup

  1. customthe solvent was evaporated in a rotary evaporator under water
  2. waitunder oil pump at 50° C. for 1 h
  3. additionThe residue was then diluted with water (500 mL)
  4. filtrationthe precipitate recovered by filtration
  5. washwashed with more water
  6. dry with materialdried in dessicator over P2O5

Sources & evidence

ORD record
ord-3558e945cd5b4334af03bf57508d41b6
Source dataset
uspto-grants-2005_07
Patent number
US06916949B2

Reaction notes

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