Sodium Hydroxide → HCID 21833668, compound

HRID 1418716Notes

Reaction equation

HRID 1418716 reaction equation
CC(C)(C)C([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[CH:8][C:7]=1[Cl:18])=O.[OH-].[Na+]>C(O)C>[Cl:18][C:7]1[CH:8]=[C:9]([CH2:12][N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)[CH:10]=[CH:11][C:6]=1[OH:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 545168712-Chloro-4-(1-pyrazolyl)methylphenyl 2,2-dimethylpropanoate

Product 1

HCID 21833668HCID 21833668, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 20.0 g of 2-chloro-4-(1-pyrazolyl)methylphenyl 2,2-dimethyl-propanoate, 50 ml of 20% aqueous sodium hydroxide solution and 300 ml of ethanol was heated at reflux for 5 hours. The reaction mixture was then concentrated under reduced pressure, to which water was added, and the mixture was adjusted to pH 6.0 with concentrated hydrochloric acid. This mixture was extracted with ethyl acetate. The organic layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 11.5 g of 2-chloro-4-(1-pyrazolyl)methylphenol as white crystals. Yield, 80.7%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. concentrationThe reaction mixture was then concentrated under reduced pressure, to which water
  4. additionwas added
  5. extractionThis mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dcac54f3e76b46d78db06729f36075f7
Source dataset
uspto-grants-1999_03
Patent number
US05883262

Reaction notes

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