Sodium Azide → 2-Azido-1-(3,4-dihydroxyphenyl)ethanone

HRID 234143Notes

Reaction equation

HRID 234143 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([OH:12])[C:8](=[CH:10][CH:11]=1)[OH:9])=[O:4].[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:13]([CH2:2][C:3]([C:5]1[CH:6]=[C:7]([OH:12])[C:8](=[CH:10][CH:11]=1)[OH:9])=[O:4])=[N+:14]=[N-:15]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 668342-Chloro-3',4'-dihydroxyacetophenone

Product 1

HCID 214660312-Azido-1-(3,4-dihydroxyphenyl)ethanoneYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 4-chloroacetylcatechol (25 g) in DMF (200 ml) was added sodium azide (10.5 g), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. After the solvent was evaporated, the solids thus obtained was washed with a solution of n-hexane:ether=5:1 to give 23.2 g of 4-azidoacetylcatechol (yield, 90%).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter the solvent was evaporated
  4. customthe solids thus obtained
  5. washwas washed with a solution of n-hexane

Sources & evidence

ORD record
ord-afab536b3d874b7c898e921e9c48c510
Source dataset
uspto-grants-1997_01
Patent number
US05594004

Reaction notes

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