Thionyl Chloride → 5-Methylfuran-2-carbonyl chloride

HRID 967016Notes

Reaction equation

HRID 967016 reaction equation
O=S(Cl)[Cl:3].[CH3:5][C:6]1[O:10][C:9]([C:11]([OH:13])=O)=[CH:8][CH:7]=1>C1C=CC=CC=1>[CH3:5][C:6]1[O:10][C:9]([C:11]([Cl:3])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 747102-Furancarboxylic acid, 5-methyl-

Product 1

HCID 27598515-Methylfuran-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 0.31 g of SOCl2 in 2 ml of benzene was added dropwise at 0° C. under nitrogen atmosphere to a solution of 0.22 g of 5-methylfuran-2-carboxylic acid, prepared following the method described by Robert et al., Eur. J. Med. Chem. 30, 915-924 (1995), in 5 ml of benzene. The mixture was stirred at 80° C. for 1 hour and the excess SOCl2 was then distilled off. The residue (0.24 g, 97% of theory) was utilized for the next step without further purification.

Workup

  1. customprepared
  2. distillationthe excess SOCl2 was then distilled off
  3. customThe residue (0.24 g, 97% of theory) was utilized for the next step without further purification

Sources & evidence

ORD record
ord-575325239ad44fc688d9e98375445e21
Source dataset
uspto-grants-2005_10
Patent number
US06953800B2

Reaction notes

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