Methanol → HCID 22168556, compound

HRID 1824607Notes

Reaction equation

HRID 1824607 reaction equation
CS[C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7].[OH:18][S:19]([O-:22])(=O)=O.[K+].[CH3:24]O>O>[CH3:24][S:19]([C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7])(=[O:22])=[O:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 516920Potassium bisulfateHCID 22168635HCID 22168635, compound

Product 1

HCID 22168556HCID 22168556, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Allyl 3-methylthio-5-nitrobenzoate (1.12 g, 4.4 mM) was dissolved in methanol (30 ml), and cooled to 2°. A solution of “potassium peroxymonopersulfate” (2 KHSO5.KHSO4.K2SO4, 8.13 g, 13.2 mM) in water (25 ml) was added slowly, and stirring continued for 4 hours. The mixture was diluted with water (60 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water, brine, and dried over Na2SO4. Crude product was purified by chromatography on silica using a gradient of petrol/ethyl acetate (3:1 to 2:1) to give allyl 3-methylsulphonyl-5-nitrobenzoate (0.74 g, 59%). Nmr (DMSO-d6): δ 3.44 (s, 3H); 4.94 (dt, 2H); 5.32-5.53 (m, 2H); 6.01-6.25 (m, 1H); 8.78 (t, 1H); 8.89 (t, 1H); 8.91 (t, 1H).

Workup

  1. temperaturecooled to 2°
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customCrude product was purified by chromatography on silica using a gradient of petrol/ethyl acetate (3:1 to 2:1)

Sources & evidence

ORD record
ord-27513ac11cf0426fb6ca4a773d496461
Source dataset
uspto-grants-2006_05
Patent number
US07041836B2

Reaction notes

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