Methanol → HCID 14249922, compound

HRID 867750Notes

Reaction equation

HRID 867750 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:11])=[CH:5][C:6]=1[CH2:7][C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:1][C:2]1[S:3][C:4]([CH3:11])=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH3:17])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 142499212,5-Dimethyl-3-thiopheneacetic acid

Product 1

HCID 14249922HCID 14249922, compoundYield 90%

Procedure

A solution of 2,5-dimethyl-3-thiophene acetic acid (34 g, 0.200 mol) and concentrated sulfuric acid (1.0 ml) in MeOH (500 ml) was stirred at room temperature for 16 hours. The mixture was concentrated in vacuo, diluted to 500 ml with H2O, and neutralized with solid NaHCO3. The product was extracted with Et2O (2×200 ml), the organic layer was washed with H2O (1×100 ml), dried over MgSO4, and treated with activated charcoal. The solvent was removed in vacuo to give the product (33.2 g, 90% yield) as an oil; IR (neat) 1750 cm-1 ; mass spectrum m/z 184 (M+); 1H NMR (CDCl3) δ 2.32 (s, 3H, thiophene-CH3), 2.38 (s, 3H, thiophene-CH3), 3.45 (s, 2H, CH2CO2), 3.67 (s, 3H, CO2CH3), 6.53 (s, 1H, thiophene-H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted to 500 ml with H2O
  3. extractionThe product was extracted with Et2O (2×200 ml)
  4. washthe organic layer was washed with H2O (1×100 ml)
  5. dry with materialdried over MgSO4
  6. additiontreated with activated charcoal
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a02a7db960df4c818fc334262c472baf
Source dataset
uspto-grants-1988_10
Patent number
US04775757

Reaction notes

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