Benzene → Ethyl [4-(butyliminomethylene)phenoxy]acetate

HRID 579995Notes

Reaction equation

HRID 579995 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[CH2:16]([NH2:20])[CH2:17][CH2:18][CH3:19].C1C=CC=CC=1>O>[CH2:16]([N:20]=[C:1]=[C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH2:4]1)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 241BenzeneHCID 8007ButylamineHCID 291358Ethyl 2-(4-formylphenoxy)acetate

Product 1

HCID 23199953Ethyl [4-(butyliminomethylene)phenoxy]acetateYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ethyl (4-formylphenoxy)acetate (104.1 g, 0.5 mole), butylamine (36.6 g, 0.5 mole) and benzene (400 ml) were united and refluxed in a flask equipped with a Dean-Stark water separator. After one hour, water ceased to separate. The heating was terminated after 6 hours and the mixture distilled. There was obtained 108.6 g of product boiling at 178°-181° C. at 0.5 mm Hg pressure.

Workup

  1. temperaturerefluxed in a flask
  2. customto separate
  3. customThe heating was terminated after 6 hours
  4. distillationthe mixture distilled

Sources & evidence

ORD record
ord-b387a4b205e5461bb0fe3b0a3780cf3f
Source dataset
uspto-grants-1988_06
Patent number
US04751244

Reaction notes

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