Water → Methyl 4-(3-chloropropylsulfonyl)benzoate

HRID 73007ノート

反応式

HRID 73007 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.[OH2:16].[OH:17]OS([O-])=O.[K+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)(=[O:17])=[O:16]

参加物

5

反応物 3

HCID 962WaterHCID 13749599Methyl 4-(3-chloropropylthio)benzoateHCID 23707502Potassium hydroxy sulfite

生成物 1

HCID 68290846Methyl 4-(3-chloropropylsulfonyl)benzoate収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Methyl 4-(3-chloropropylsulfanyl)benzoate (1.84 g, 7.52 mmol) was dissolved in methanol (46 mL), followed by the addition of water (4.6 mL) and Oxone (4.62 g, 7.52 mmol). The reaction mixture was stirred at room temperature for 14 h. The reaction mixture was filtered and the solvent removed in vacuo. The resulting solid was dissolved in dichloromethane and washed with water (2×10 mL). The organic layer was dried over Na2SO4, filtered and the solvent removed in vacuo to yield methyl 4-(3-chloropropylsulfonyl)benzoate (1.89 g, 91%) as a viscous liquid. ESI-MS m/z calc. 276.0. Found 277.1 (M+1)+; Retention time: 1.36 minutes (3 min run). 1H NMR (400 MHz, DMSO-d6) δ 8.21 (d, J=8.3 Hz, 2H), 8.07 (d, J=8.3 Hz, 2H), 3.92 (s, 3H), 3.73-3.46 (m, 4H), 2.21-1.79 (m, 2H).

後処理

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed in vacuo
  3. dissolutionThe resulting solid was dissolved in dichloromethane
  4. washwashed with water (2×10 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-9df480654b1e4d26909981dd18a482de
出典データセット
uspto-grants-2014_09
特許番号
US08828996B2

反応ノート

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