Dichloromethane → 3-(Methylsulfonyl)phenol

HRID 991634

反応式

HRID 991634 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 6375563-(Methylsulfonyl)phenol収率 45.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21908982Water methylene chloride溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  1. customevaporated to dryness
  2. additionAqueous H2SO4 (60%; 10 mL) was added to the residue
  3. customto come to room temperature
  4. extractionExtraction with CH2Cl2
  5. customdrying
  6. concentration(MgSO4), and concentration

出典と根拠

ORDレコード
ord-b14b87f5bb384528ab0bafa84a3ffdc1
出典データセット
uspto-grants-2002_10
特許番号
US06465467B1

関連ノート

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