Aniline → 4-Hydroxydiphenylamine

HRID 2354037Notes

Reaction equation

HRID 2354037 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(=[O:15])[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1.C(N(CC)CC)C>C(O)C>[OH:15][C:8]1[CH:9]=[CH:10][C:11]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 125111,4-Cyclohexanedione

Product 1

HCID 312084-HydroxydiphenylamineYield 27.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.93 g of aniline, 2.24 g of 1,4-cyclohexanedione and 1.4 ml of triethylamine were heated with stirring in 15 ml of ethanol at 50° C. to 60° C. and reacted in air for 8 hours. During the reaction, ethanol was added as needed. After concentrating the reaction mixture under reduced pressure, the resultant was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) and 0.50 g of N-(4-hydroxyphenyl)aniline was obtained (yield 27.4%).

Workup

  1. customreacted in air for 8 hours
  2. additionwas added
  3. concentrationAfter concentrating the reaction mixture under reduced pressure
  4. customthe resultant was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-44dc6663f00845ad8160334a997c3594
Source dataset
uspto-grants-2010_07
Patent number
US07750156B2

Reaction notes

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