Methylparaben → 4-(6-Chloro-pyridazin-3-yloxy)-benzoic acid methyl ester

HRID 215836Notes

Reaction equation

HRID 215836 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[Cl:18][C:19]1[N:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=1>C1COCC1.O>[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:22]2[N:21]=[N:20][C:19]([Cl:18])=[CH:24][CH:23]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 7456MethylparabenHCID 673313,6-DichloropyridazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 606748904-(6-Chloro-pyridazin-3-yloxy)-benzoic acid methyl esterYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (0.87 g, 7.75 mmol) was added in portions to a solution of 4-hydroxybenzoic acid methyl ester 1 (1.15 g, 7.56 mmol) in anhydrous THF (25 ml). The mixture was stirred at room temperature for 30 minutes, then 3,6-dichloro-pyridazine (1.12 g, 7.56 mmol) was added. The reaction mixture was stirred at room temperature for 1 h and heated at reflux for 14 h. The mixture was cooled to room temperature and diluted with water (100 ml). The formed precipitate was collected by filtration, washed with water and dried to obtain 1.315 g (66%) of 4-(6-chloro-pyridazin-3-yloxy)-benzoic acid methyl ester which was used for the next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. temperatureheated
  3. temperatureat reflux for 14 h
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationThe formed precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-f51d8c5533534c11a21084511f6f8491
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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