Sodium Hydroxide → 4-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone

HRID 579263Notes

Reaction equation

HRID 579263 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:30])[N:14]([CH3:29])[N:15]=[C:16]([CH3:28])[C:17]=1S(C1C=CC(C)=CC=1)(=O)=O)[CH3:2].[OH-:31].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:30])[N:14]([CH3:29])[N:15]=[C:16]([CH3:28])[C:17]=1[OH:31])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 666955404-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-(4-methylphenylsulfonyl)-2,3-dihydro-3-pyridazinone

Product 1

HCID 546837784-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinoneYield 35.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

To a 10 ml volume two-necked flask with Dean-Start, 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-(4-methylphenylsulfonyl)-2,3-dihydro-3-pyridazinone ((2-36)-(1)-39) (699 mg), toluene (2.45 ml), tetrabutylammonium bromide (27 mg), and 48 w/w % of aqueous sodium hydroxide solution (550 mg) were added. Water was removed by azeotropic distillation under reflux for 33 hours. After the mixture was cooled to room temperature, water was added, and the organic layer was removed. To the aqueous layer, 20 w/w % of sulfuric acid was added to adjust pH to 4, and extracted with toluene 2 times. The organic layers were combined, and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane: ethyl acetate=5:1) to give 169 mg of 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone ((1-4)-(1)-39).

Workup

  1. customWater was removed by azeotropic distillation
  2. temperatureunder reflux for 33 hours
  3. additionwater was added
  4. customthe organic layer was removed
  5. additionTo the aqueous layer, 20 w/w % of sulfuric acid was added
  6. extractionextracted with toluene 2 times
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-888f52ed2d154a5c86f83afdd500caa3
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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