Methanol → HCID 22729265, compound

HRID 2085162Notes

Reaction equation

HRID 2085162 reaction equation
COC[O:4][C:5]1[C:13]2[CH:12]=[C:11]([C:14]([OH:16])=[O:15])[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.S(Cl)(Cl)=O.[CH3:21]O>>[OH:4][C:5]1[C:13]2[CH:12]=[C:11]([C:14]([O:16][CH3:21])=[O:15])[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 22728980HCID 22728980, compound

Product 1

HCID 22729265HCID 22729265, compound

Procedure

4-(Methoxymethyloxy)benzo(b)thiophene-2-carboxylic acid (7 g) was dissolved in methanol (140 ml) and thionyl chloride (2.0 ml) was added under ice-cooling. The mixture was refluxed under heating for 2 hr and the reaction mixture was concentrated under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and after filtration, the solvent was evaporated under reduced pressure to give the title compound (6.0 g).

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed
  3. temperatureunder heating for 2 hr
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionWater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationafter filtration
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9eda75e5b12f4543834364544b51ae66
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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