Water → 3-Phenoxybenzylidene-3-pentylamine

HRID 224272Notes

Reaction equation

HRID 224272 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].O.[C:23]1(C)[CH:28]=[CH:27]C=[CH:25][CH:24]=1>>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[N:12][CH:23]([CH2:28][CH3:27])[CH2:24][CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 10948363-Phenoxy-benzylamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 541965723-Phenoxybenzylidene-3-pentylamineYield 92.5%

Procedure

60.5 g (0.226 mol) of N-3-pentylidene-(3-phenoxybenzylamine is dissolved in 50 ml of toluene; to the solution is then added 2 g (0.0179 mol) of potassium tert-butylate, and the mixture is refluxed for 4 hours. After cooling of the reaction mixture, extraction is effected by shaking with 50 ml of water, and the organic phase is separated in a separating funnel. The toluene is distilled off in a slight water-jet vacuum to leave 56 g (0.21 mol) of 3-phenoxybenzylidene-3-pentylamine, corresponding to a yield of 92.5% of theory; b.p. 125° C./Pa.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureAfter cooling of the reaction mixture, extraction
  3. customthe organic phase is separated in a separating funnel
  4. distillationThe toluene is distilled off in a slight water-jet vacuum

Sources & evidence

ORD record
ord-3439b05be3fb448892a37c3c50632909
Source dataset
uspto-grants-1980_11
Patent number
US04231962

Reaction notes

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