1,3-Cyclohexanedione → HCID 21994440, compound

HRID 1977598Notes

Reaction equation

HRID 1977598 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH:5][C:11]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH:12]=1

Participants

5

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 743145-Amino-2-methoxyphenol

Product 1

HCID 21994440HCID 21994440, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 1.00 g (7.19 mmole) of 3-hydroxy-4-methoxyaniline, 0.83 g (7.19 mmole) of 1,3-cyclohexanedione, and 50 mg of p-toluenesulfonic acid in 20 ml of benzene were heated reflux for 4.5 hours. The reaction solution was allowed to stand for one night at room temperature and the precipitated brown solid was collected by suction filtration. The crystal was washed with benzene, then was dried in vacuo to obtain 3-(3-hydroxy-4-methoxyanilino)-2-cyclohexen-1-one 1.68 g (yield 100%).

Workup

  1. temperaturereflux for 4.5 hours
  2. waitto stand for one night at room temperature
  3. filtrationthe precipitated brown solid was collected by suction filtration
  4. washThe crystal was washed with benzene
  5. customwas dried in vacuo

Sources & evidence

ORD record
ord-d6ec3dea548e4a4a81444f4b1202ce41
Source dataset
uspto-grants-2001_05
Patent number
US06235736B1

Reaction notes

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