Tetronic acid → HCID 54244004, compound

HRID 982405Notes

Reaction equation

HRID 982405 reaction equation
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].[C:8]([C:11]1[S:15][C:14]([CH:16]=O)=[CH:13][CH:12]=1)([OH:10])=[O:9]>C1COCC1>[C:8]([C:11]1[S:15][C:14]([CH:16]=[C:1]2[C:2](=[O:3])[CH2:4][O:5][C:6]2=[O:7])=[CH:13][CH:12]=1)([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 521261Tetronic acidHCID 8188825-Formyl-2-thiophenecarboxylic Acid

Product 1

HCID 54244004HCID 54244004, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As before, 0.571 gm of tetronic acid (FW=100, 5.7 mmole) was reacted with 2.2 equiv. or 1.96 gm of 5-carboxy-2-thiophenecarboxaldehyde with 6 mL of THF and 10.5 mL of conc. HC1 and applied heat. A greenish precipitate formed immediately. Stirring was continued for 10 minutes. Workup and recrystallization from methanol gave 0.91 gm (67%) of the product having a M. p. of approximately 255°-268° C. and a molecular formula of C10H6O5S: calculated %C 50.42; %H 2.54; found %c 50.22; %H 2.75.

Workup

  1. temperatureapplied heat
  2. customA greenish precipitate formed immediately
  3. customWorkup and recrystallization from methanol

Sources & evidence

ORD record
ord-fd61a43df35c495dac2a7857273b84a8
Source dataset
uspto-grants-1991_02
Patent number
US04996227

Reaction notes

Loading…