Trichloroisocyanuric Acid → 4-Methylcatechol

HRID 57322

Reaction equation

HRID 57322 reaction equation
C1(N(Cl)[C:7](=[O:8])N(Cl)C(=O)N1Cl)=O.F[C:14]1C=[CH:18][C:17]([CH3:20])=[C:16]([N+]([O-])=O)[CH:15]=1.CC(O)=[O:26].OS(O)(=O)=O>>[CH3:20][C:17]1[CH:18]=[C:7]([OH:8])[C:14](=[CH:15][CH:16]=1)[OH:26]

Participants

4

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 679654-Fluoro-2-nitrotolueneHCID 23350293Acetic acid sulfuric acid

Product 1

HCID 99584-MethylcatecholYield 33.1%

Conditions

Temperature
70 °C

Procedure

TCCA (16.7 g, 72 mmol) was added to a solution of 4-fluoro-1-methyl-2-nitrobenzene (12.4 g, 80 mmol) in CH3CO2H/H2SO4 (80 mL/80 mL). The mixture was heated to 70° C. and stirred overnight. After cooling to room temperature, the reaction mixture was poured into ice water (1000 mL) and extracted with DCM (2×200 mL). The combined organic phase was washed with brine and concentrated in vacuo. The residue was purified by column chromatography (PE: EA=50:1) to give compound 1 (5.0 g, 33.1%) as a yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with DCM (2×200 mL)
  3. washThe combined organic phase was washed with brine
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (PE: EA=50:1)

Sources & evidence

ORD record
ord-6a5d8e0b4f2f48f6baff74346c1a6d6d
Source dataset
uspto-grants-2016_09
Patent number
US09434724B2

Linked notes

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