Hydrochloric Acid → 3-Chloro-4-methylphenyl isopropyl sulfone

HRID 2255807

反応式

HRID 2255807 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[Cl:19]Cl.Cl.N#N>O>[CH:11]([S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[C:7]([Cl:19])[CH:6]=1)(=[O:10])=[O:9])([CH3:13])[CH3:12]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 1118Sulfuric AcidHCID 24526ChlorineHCID 8167921-(Isopropylsulfonyl)-4-methylbenzene

生成物 1

HCID 197386523-Chloro-4-methylphenyl isopropyl sulfone収率 57.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
20 °C

実験手順

99.1 g (0.5 mol) of isopropyl 4-methylphenyl sulfone in 180 g of 96% strength sulfuric acid are introduced into a 500 ml glass flask equipped with stirrer, condenser, gas inlet, thermometer and dropping funnel. At 70° C., about 140 g of chlorine are metered in over the course of 6 hours with vigorous stirring. After the reaction is completed, residual hydrogen chloride is eliminated by passing a N2 stream through the flask, 300 g of water are added dropwise and the mixture is allowed to cool to 20° C. in the course of 2 hours with stirring. The mixture is extracted four times each with 200 g of methylene chloride, the combined extracts are washed to neutrality using 5% strength NaHCO3 solution, dried with Na2SO4 and concentrated on a rotary evaporator. 66.7 g of 3-chloro-4-methylphenyl isopropyl sulfone are obtained (yellowish oil, content 94.3% by weight, corresponding to a yield of 54.1%, 1H-NMR (CDCl3): 7.3-7.9 (m, 3H); 3.23 (sp, 6.8 Hz, lH); 2.47 (s); 1.42 d, 6.8 Hz, 6H).

後処理

  1. customequipped with stirrer, condenser, gas inlet
  2. customAt 70° C.
  3. customare metered in over the course of 6 hours with vigorous stirring
  4. additionare added dropwise
  5. extractionThe mixture is extracted four times each with 200 g of methylene chloride
  6. washthe combined extracts are washed
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated on a rotary evaporator

出典と根拠

ORDレコード
ord-78c1baff4ff14773940799127fcf53d5
出典データセット
uspto-grants-1993_08
特許番号
US05241120

関連ノート

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