Sulfuric Acid → 2-Methylbenzo[b]thiophene-5-carboxylic acid methyl ester

HRID 1072829Notes

Reaction equation

HRID 1072829 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]2[S:8][C:9]([CH3:11])=[CH:10][C:6]=2[CH:5]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[C:19](=O)([O-])O.[Na+]>CO>[CH3:19][O:2][C:1]([C:4]1[CH:13]=[CH:12][C:7]2[S:8][C:9]([CH3:11])=[CH:10][C:6]=2[CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 1366303686792-71-4

Product 1

HCID 136630372-Methylbenzo[b]thiophene-5-carboxylic acid methyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Carboxy-2-methylbenzo[b]thiophene (2.1 g, 10.9 mmol) was dispersed in methanol (50 ml), and concentrated sulfuric acid was added. The mixture was refluxed with heating for 6 hr. After cooling, a saturated aqueous solution of sodium hydrogencarbonate was added, and methanol was distilled away under reduced pressure. The residue was extracted with methyl t-butyl ether. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure to give the objective compound (2.0 g, 89%) as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 6 hr
  3. temperatureAfter cooling
  4. distillationmethanol was distilled away under reduced pressure
  5. extractionThe residue was extracted with methyl t-butyl ether
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe desiccant was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-52dc703674ef45a891564ee44efb47ea
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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