Hydrochloric Acid → 5-Benzyl-2-furoic acid

HRID 894233Notes

Reaction equation

HRID 894233 reaction equation
[C:1]([C:9]1[O:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.[OH-].[K+].Cl>O.C(O)CO>[CH2:1]([C:9]1[O:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 28772555-Benzoylfuran-2-carboxylic acid

Product 1

HCID 28322525-Benzyl-2-furoic acidYield 63.6%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

5-Benzoylfuran-2-carboxylic acid [420 mg.; Knoppova et al. Collect. Czech. Chem. Commun. 42, 3175-9 (1977), Chem. Abs. 88, 169842d] was combined with 10 ml. of hydrazine, 1.5 g. of potassium hydroxide and 10 ml. of ethylene glycol and heated for 1.5 hours in an oil bath maintained at 160° C. The mixture was cooled in an ice-water bath, diluted with water and acidified with conc. hydrochloric acid. Filtration gave 5-benzylfuran-2-carboxylic acid (250 mg., m/e 202).

Workup

  1. temperatureThe mixture was cooled in an ice-water bath
  2. filtrationFiltration

Sources & evidence

ORD record
ord-d0b0ed8c215249d0b0cc35f65a543bc0
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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