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Acetic Acid → 2-Methoxy-4-(methylsulfonyl)benzoic acid

HRID 452445
ノート
印刷プレビュー

反応式

HRID 452445 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10](SC)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].OO.[S:16]([O-:19])([O-])=[O:17].[Na+].[Na+].Cl.[C:23](O)(=O)C>O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([S:16]([CH3:23])(=[O:19])=[O:17])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 6433294-(Methylthio)-o-anisic acid

生成物 1

HCID 144781692-Methoxy-4-(methylsulfonyl)benzoic acid

試薬・触媒・溶媒 1

HCID 962
Water
溶媒
2 回

反応条件

温度
10 °C

実験手順

2-methoxy-4-(methylthio)benzoic acid (10.8 g, 54 mmol) is dissolved in acetic acid and the solution was cooled to 10° C. Sodium tungstate 2-hydrate (1.2 g, 3.7 mmol) was added until percipitation. After the precipitation had dissolved and the solution was cooled H2O2 (4.1 ml, 135 mmol) was added dropwise. 10 minutes later the reaction mixture was heated to 50° C. for 1 h. Sodium sulphite (3.4 g, 27 mmol) in water (80 ml) was added and the resulting mixture was stirred for 30 min. Water and aqueous HCl (10%) were added. The aqueous phase was extracted with EtOAc and the combined organic layers were dried (Na2SO4) and evaporated under reduced pressure to give a white powder (5.7 g). No further purification was made of this intermediate. 1H-NMR (400 MHz, MeOH): δ 7.92 (1H, d, J 8 Hz), δ 7.61 (1H, s), δ 7.56 (1H, d, J 8 Hz), δ 3.95 (3H, s), δ 3.18 (3H, s).

後処理

  1. customAfter the precipitation
  2. dissolutionhad dissolved
  3. additionwas added dropwise
  4. temperature10 minutes later the reaction mixture was heated to 50° C. for 1 h
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialthe combined organic layers were dried (Na2SO4)
  7. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-cea50ee5862f457c9bdcf658cfc1a887
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08492372B2

反応ノート

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