Water → Benzenamine, 4-ethenyl-N,N-diphenyl-

HRID 625193Notes

Reaction equation

HRID 625193 reaction equation
[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[CH2:23]1COCC1>>[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[CH2:23])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 77846Benzaldehyde, 4-(diphenylamino)-

Product 1

HCID 10869403Benzenamine, 4-ethenyl-N,N-diphenyl-Yield 89%

Procedure

Thereafter, 20 g (0.066 mol) of 4-(diphenylamino)benzaldehyde (1) dissolved in 40 ml of THF was charged into the dropping funnel, and was gradually added dropwise to the mixture. After the addition, a reaction was caused at room temperature for 2 hours. Then, 70 ml of water was added thereto. The product was extracted with ethyl acetate, and the extract was washed with water until neutralized. The organic phase was dried, concentrated and then purified by column chromatography. Pale yellow crystals of 4-(diphenylamino)styrene (3) (16 g, yield: 89%) was obtained.

Workup

  1. additionwas charged into the dropping funnel
  2. additionwas gradually added dropwise to the mixture
  3. additionAfter the addition
  4. extractionThe product was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-0f4f1bd1023441afa1fafed63d9b72a5
Source dataset
uspto-grants-2016_04
Patent number
US09304417B2

Reaction notes

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