Sulfuric Acid → Methyl 5-methyl-2-furancarboxylate

HRID 1961235Notes

Reaction equation

HRID 1961235 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.OS(O)(=O)=O.[C:15]([O-])(O)=O.[Na+].[OH-].[Na+]>CO.C(Cl)(Cl)Cl>[CH3:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:15])=[O:8])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 747102-Furancarboxylic acid, 5-methyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 137628Methyl 5-methyl-2-furancarboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a 200 mL round-bottomed flask with condenser was added 5-methyl-2-furancarboxylic acid (2.5 g, 19.82 mmol) in Methanol (100 mL). H2SO4 (10.5 mL, 197 mmol) was added slowly at room temperature. The reaction mixture was heated to 50° C. overnight. The reaction mixture was cooled to 0° C. and a saturated solution of NaHCO3 was added to neutral pH followed by 5N NaOH to pH 10. CHCl3 was added and the organic phase was separated, dried with Na2SO4 and concentrated affording the title compound (2.3 g, 16.3 mmol, 82%): LC-MS (ES) m/z=141 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customthe organic phase was separated
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c91c6341b705473dbe855d0973963b7d
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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