Sodium Hydroxide → 2-chloro-4-(2-2H-1,2,3-triazolylmethyl)phenol

HRID 2292664Notes

Reaction equation

HRID 2292664 reaction equation
CC(C)(C)C([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[N: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[N:17]=[CH:16][CH:15]=[N:14]2)[CH:10]=[CH:11][C:6]=1[OH:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53869820HCID 53869820, compound

Product 1

HCID 218336772-chloro-4-(2-2H-1,2,3-triazolylmethyl)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-4-(2-2H-1,2,3-triazolyl)methylphenyl 2,2-dimethylpropanoate (3 g), 20% aqueous sodium hydroxide solution (10 ml)and ethanol (60 ml) 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 2-chloro-4-(2-2H-1,2,3-triazolylmethyl)phenol.

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-37af69cf8bc84769902228512fb10c3a
Source dataset
uspto-grants-1997_11
Patent number
US05684022

Reaction notes

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