Water → N-isobutylidene-3-phenoxybenzylamine

HRID 224268Notes

Reaction equation

HRID 224268 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].[O:6]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][NH2:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>C1(C)C=CC=CC=1>[CH:1](=[N:17][CH2:16][C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([O:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:14]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 6561IsobutyraldehydeHCID 10948363-Phenoxy-benzylamine

Product 1

HCID 23332476N-isobutylidene-3-phenoxybenzylamineYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

38 g (0.528 mol) of isobutyraldehyde is added dropwise within 30 minutes, with stirring, to a solution of 99.5 g (0.5 mol) of 3-phenoxybenzylamine in 100 ml of toluene. After completion of the dropwise addition, stirring is continued for 20 minutes at room temperature, and the water which has formed (about 8.5 g) is separated in a separating funnel. The toluene with the unreacted isobutyraldehyde and residual water is then removed by rotation in a water-jet vacuum, and the residue is distilled in an oil-pump vacuum to yield 124 g (0.49 mol) of N-isobutylidene-(3-phenoxybenzylamine) as a colourless, mobile liquid, corresponding to a yield of 97.8% of theory; b.p. 85° C./4 Pa; nD20 =1.5666.

Workup

  1. additionAfter completion of the dropwise addition
  2. customis separated in a separating funnel
  3. customThe toluene with the unreacted isobutyraldehyde and residual water is then removed by rotation in a water-jet vacuum
  4. distillationthe residue is distilled in an oil-pump vacuum

Sources & evidence

ORD record
ord-f58c8ad04f564144b885d3481a4c64b3
Source dataset
uspto-grants-1980_11
Patent number
US04231962

Reaction notes

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