Nitric Acid → HCID 59444087, compound

HRID 2060020Notes

Reaction equation

HRID 2060020 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[N+:13]([O-])([OH:15])=[O:14].O>C(Cl)Cl>[CH3:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][C:5]([N+:13]([O-:15])=[O:14])=[C:4]([OH:12])[CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 962WaterHCID 1670483-Methyl-4-(methylsulfonyl)phenol

Product 1

HCID 59444087HCID 59444087, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-4-(methylsulfonyl)phenol (D85, 503 mg, 2.29 mmol) was dissolved in DCM (5 mL) and 70% nitric acid (0.16 mL, 3.58 mmol) was added dropwise to the reaction. The mixture was stirred o/n. A further 2 mL of 70% nitric acid was then added. The reaction was stirred for 4 h, then H2O (20 mL) was added and the 2 phases were separated. The aqueous layer was extracted with DCM and the combined organics were dried (Na2SO4) and concentrated by rotary evaporation to give a yellow solid, which was purified via flash column chromatography (silica, iso-hexane to 50% EtOAc/50% iso-hexane) to give a yellow solid. This solid was triturated with Et2O (2×) to give 5-methyl-4-(methylsulfonyl)-2-nitrophenol (D86, 103 mg, 19%) as a yellow solid.

Workup

  1. stirringThe reaction was stirred for 4 h
  2. customthe 2 phases were separated
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. concentrationconcentrated by rotary evaporation
  6. customto give a yellow solid, which
  7. customwas purified via flash column chromatography (silica, iso-hexane to 50% EtOAc/50% iso-hexane)
  8. customto give a yellow solid
  9. customThis solid was triturated with Et2O (2×)

Sources & evidence

ORD record
ord-dc822e8e4ad444909fae4525bfc1e96a
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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