Hydrochloric Acid → methyl 5-(methoxymethyl)furan-2-carboxylate

HRID 1461264Notes

Reaction equation

HRID 1461264 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH2:11]C)=[O:9])=[CH:5][CH:4]=1.[CH3:13][O-:14].[Na+].Cl>CO>[CH3:13][O:14][CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 4193918methyl 5-(methoxymethyl)furan-2-carboxylateYield 82.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 20 ml of dry methanol was dissolved 5.0 g (26.5 mmol) of ethyl 5-chloromethyl-2-furancarboxylate, followed by addition of 20 ml of a 28% solution of sodium methoxide in methanol. The mixture was stirred at room temperature for 17 hours, at the end of which time it was neutralized with 1N-hydrochloric acid. The resulting precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform and the solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure to give 3.73 g (82.7%) of methyl 5-methoxymethyl-2-furancarboxylate (Compound c) as light yellow oil.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washthe solution was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-c3860d12a04b4579906956f6964ba9b0
Source dataset
uspto-grants-1991_12
Patent number
US05075301

Reaction notes

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