Chloroacetic Acid → 2-Chloro-4-(methylsulfonyl)benzoic acid

HRID 466790ノート

反応式

HRID 466790 の反応式
S([O-])([O-])=O.[Na+].[Na+].[C:7](=[O:10])(O)[O-:8].[Na+].[Cl:12][C:13]1[CH:21]=[C:20]([S:22](Cl)(=[O:24])=[O:23])[CH:19]=[CH:18][C:14]=1C(Cl)=O.[Na].Cl[CH2:28]C(O)=O.Cl>O>[Cl:12][C:13]1[CH:21]=[C:20]([S:22]([CH3:28])(=[O:24])=[O:23])[CH:19]=[CH:18][C:14]=1[C:7]([OH:8])=[O:10]

参加物

8

反応物 6

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 198147312-Chloro-4-(chlorosulfonyl)benzoyl chloride

生成物 1

HCID 7358632-Chloro-4-(methylsulfonyl)benzoic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

A 100 mL round bottom flask equipped with a reflux condenser, thermometer, and magnetic stirrer was charged with 4.6 g (37 mmol) of sodium sulfite, 12.3 g (146 mmol) of sodium bicarbonate and 40 mL of water. The resulting slurry was heated to 75° C. and 10 g (33 mmol) of 2-chloro-4-(chlorosulfonyl)benzoyl chloride was added slowly. After stirring at 75° C. for 2 hours, 6.4 g (55 mmol) of the sodium salt of chloroacetic acid was added and the reaction mixture heated at reflux for 21 hours. The cooled reaction mixture was acidified with dilute HCl and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate and evaporated to dryness to afford 7.5 g of 2-chloro-4-(methylsulfonyl)benzoic acid as a white solid. This material was shown to be 87% pure, representing an 85% overall yield.

後処理

  1. customA 100 mL round bottom flask equipped with a reflux condenser
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux for 21 hours
  4. customThe cooled reaction mixture
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. customevaporated to dryness

出典と根拠

ORDレコード
ord-33da43ba6fa34bbb8c11c238a64efe5a
出典データセット
uspto-grants-1992_10
特許番号
US05157150

反応ノート

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