Dichloromethane → 3-(Methylsulfonyl)phenol

HRID 1789703

Reaction equation

HRID 1789703 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](N)[CH:7]=1)(=[O:5])=[O:4].[OH-].[Na+].C(Cl)Cl.N([O-])=[O:19].[Na+]>O.C(Cl)Cl.O>[CH3:2][S:3]([C:6]1[CH:7]=[C:8]([OH:19])[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27351793-(Methylsulfonyl)aniline hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 6375563-(Methylsulfonyl)phenolYield 45.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared by a slightly modified literature procedure.*3-aminophenyl methyl sulfone hydrochloride (1.18 g, 5.70 mmol) was suspended in water/CH2Cl2. The mixture was neutralized with 25% aqueous NaOH. The CH2Cl2 layer was isolated and evaporated to dryness. Aqueous H2SO4 (60%; 10 mL) was added to the residue and the solution was cooled to 0° C. A solution of NaNO2 (0.345 g, 5.00 mmol) in water (5 mL) was added dropwise. The solution was stirred at 0° C. for 30 min. and at 90° C. for 30 min. The reaction mixture was allowed to come to room temperature. Extraction with CH2Cl2, drying (MgSO4), and concentration gave 0.39 g (40%) of the title compound as a solid. MS m/z 172 (M)+. HRMS m/z calcd for C7H8O3S (M)+172.0194, found 172.0198.

Workup

  1. customThe title compound was prepared by a slightly modified literature procedure
  2. customevaporated to dryness
  3. additionAqueous H2SO4 (60%; 10 mL) was added to the residue
  4. customto come to room temperature
  5. extractionExtraction with CH2Cl2
  6. customdrying
  7. concentration(MgSO4), and concentration

Sources & evidence

ORD record
ord-45c3ff1bfa84413d9285baf79542ac92
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Linked notes

Loading…