Hydrochloric Acid → Methyl 2-methoxy-5-methylsulfinylbenzoate

HRID 637126Notes

Reaction equation

HRID 637126 reaction equation
[CH3:1][O:2][C:3]1C=[CH:11][C:10](C)=[CH:9][C:4]=1C(OC)=S.[Br-].[Br-].[Br-].[C:17]1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[S:47](=[O:50])(O)[O-].[Na+].Cl.[C:53]([O:56][CH2:57]C)(=[O:55])[CH3:54]>O.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:9][C:10]([S:47]([CH3:17])=[O:50])=[CH:11][C:54]=1[C:53]([O:56][CH3:57])=[O:55]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 23665763Sodium BisulfiteHCID 53727199Methyl 2-methoxy-5-methylthiobenzoate

Product 1

HCID 18464431Methyl 2-methoxy-5-methylsulfinylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1049PyridineSolvent

Procedure

Combine methyl 2-methoxy-5-methylthiobenzoate (3.0 g, 14.1 mmol), pyridine (10 mL) and water (10 mL). Cool in an ice bath. Add portionwise phenyltrimethylammonium tribromide (5.84 g, 15.5 mmol). After 30 minutes, warm to ambient temperature. After 3 hour, add a solution of sodium bisulfite (1.6 g) in water (4 mL). After 10 minutes, add a 12 M aqueous hydrochloric acid solution (11 mL) and water. Extract the reaction mixture four times with dichloromethane. Combine the organic layers, extract with brine, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give methyl 2-methoxy-5-methylsulfinylbenzoate: mp; 64-66° C. Elemental Analysis calculated for C9H12O4S: C, 52.62; H, 5.30. Found: C, 52.51; H, 5.37.

Workup

  1. temperatureCool in an ice bath
  2. waitAfter 3 hour
  3. waitAfter 10 minutes
  4. extractionExtract the reaction mixture four times with dichloromethane
  5. extractionextract with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue

Sources & evidence

ORD record
ord-0a2282682afb4f8e82257f0ac6529bf9
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

Loading…