N-Methylaniline → Phenol, 4-(methylphenylamino)-

HRID 2354036Notes

Reaction equation

HRID 2354036 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]1(=[O:16])[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.C(N(CC)CC)C>C(O)C>[OH:16][C:9]1[CH:10]=[CH:11][C:12]([N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 125111,4-Cyclohexanedione

Product 1

HCID 11629785Phenol, 4-(methylphenylamino)-Yield 32.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.07 g of N-methylaniline, 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 the completion of the reaction, the reaction mixture was concentrated under reduced pressure and the resultant was separated by silica gel column chromatography (n-hexane:ethyl acetate=3:1) and 0.64 g of N-(4-hydroxyphenyl)-N-methylaniline was obtained (yield 32.1%).

Workup

  1. customreacted in air for 8 hours
  2. additionwas added
  3. customAfter the completion of the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customthe resultant was separated by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-8b7c4fb270bf4436b86dfd22442c2e9e
Source dataset
uspto-grants-2010_07
Patent number
US07750156B2

Reaction notes

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