Dibenzylamine → Phenol, p-(dibenzylamino)-

HRID 2354038Notes

Reaction equation

HRID 2354038 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1(=O)[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1>C(O)C.[C].[Pd]>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 7656DibenzylamineHCID 125111,4-Cyclohexanedione

Product 1

HCID 81978Phenol, p-(dibenzylamino)-Yield 57.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1.97 g of dibenzylamine, 1.68 g of 1,4-cyclohexanedione and 40 mg of 10% palladium-carbon were heated with stirring in 40 ml of ethanol at 50° C. to 60° C. and reacted for 8 hours under air bubbling. During the reaction, ethanol was added as needed. After the completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The resultant was purified by silica gel column chromatography (n-hexane:ethyl acetate=30:1) and further separated by silica gel column chromatography (n-hexane:ethyl acetate=10:1), and 1.67 g of N-(4-hydroxyphenyl)dibenzylamine was obtained (yield 57%).

Workup

  1. customreacted for 8 hours under air
  2. custombubbling
  3. customDuring the reaction, ethanol
  4. additionwas added
  5. customAfter the completion of the reaction
  6. customthe catalyst was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resultant was purified by silica gel column chromatography (n-hexane:ethyl acetate=30:1)
  9. customfurther separated by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-8b3ba28b76d44748b28cddab0b1f661f
Source dataset
uspto-grants-2010_07
Patent number
US07750156B2

Reaction notes

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