Water → Methyl 4-(3-chloropropylsulfonyl)benzoate

HRID 73007Notes

Reaction equation

HRID 73007 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 68290846Methyl 4-(3-chloropropylsulfonyl)benzoateYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9df480654b1e4d26909981dd18a482de
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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