Hydrochloric Acid → Ethyl 5-(chloromethyl)-2-furancarboxylate

HRID 1809966Notes

Reaction equation

HRID 1809966 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7].C=O.Cl.[Cl:14][CH2:15]Cl>[Cl-].[Zn+2].[Cl-]>[Cl:14][CH2:15][C:5]1[O:1][C:2]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6344DichloromethaneHCID 11980Ethyl 2-furoate

Product 1

HCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To a solution of 100 g (0.71 M) of ethyl 2-furoate in 250 ml of dichloromethane are added 30.6 g (1.02 M) of paraformaldehyde and 25.4 g (0.19 M) of zinc chloride. Gaseous hydrogen chloride is passed into the reaction medium. An exothermic reaction is observed, and the temperature reaches 35° C. The evolution of gas is maintained up to the end of the reaction, which is monitored by thin-layer chromatography (TLC). The product obtained is then purified by chromatography on silica using dichloromethane as eluent, to give 134.6 g of ethyl 5-chloromethylfuran-2-carboxylate in the form of a colourless oil.

Workup

  1. customAn exothermic reaction
  2. customreaches 35° C
  3. temperatureThe evolution of gas is maintained up to the end of the reaction, which
  4. customThe product obtained
  5. customis then purified by chromatography on silica

Sources & evidence

ORD record
ord-26772d103f31478ab210f521e31a0b9c
Source dataset
uspto-grants-2013_01
Patent number
US08362057B2

Reaction notes

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