Glyoxylic Acid → trans-3-(2-Thenoyl)acrylic Acid

HRID 126991

Reaction equation

HRID 126991 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.[C:6]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)(=[O:8])[CH3:7]>O>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:6](=[O:8])/[CH:7]=[CH:2]/[C:1]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 760Glyoxylic Acid2×HCID 69202-Acetylthiophene

Product 1

HCID 5773483trans-3-(2-Thenoyl)acrylic AcidYield 52.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
125 °C

Procedure

A two phase mixture of 18 grams glyoxylic acid (an 80% solution of glyoxylic acid in water) and 25.2 grams of 2-acetylthiophene is heated to 125° C. with stirring, and heating and stirring are maintained for about 5 hours. A clear solution forms at 115° C. and the water formed is removed by means of a Dean-Stark apparatus. On cooling the residue solidifies. It is dissolved in 100 cc ether and extracted with 150 cc of a 20% solution of Na2CO3. This aqueous solution is treated with activated charcoal, filtered and made strongly acid with 20% HCl. The solid is filtered and dissolved in about 1 L ether. The ether is dried over MgSO4 and removed to yield 19.1 g of the title compound, melting point 139°-142° C.

Workup

  1. temperatureheating
  2. stirringstirring
  3. temperatureare maintained for about 5 hours
  4. customis removed by means of a Dean-Stark apparatus
  5. temperatureOn cooling the residue solidifies
  6. dissolutionIt is dissolved in 100 cc ether
  7. extractionextracted with 150 cc of a 20% solution of Na2CO3
  8. additionThis aqueous solution is treated with activated charcoal
  9. filtrationfiltered
  10. filtrationThe solid is filtered
  11. dissolutiondissolved in about 1 L ether
  12. dry with materialThe ether is dried over MgSO4
  13. customremoved

Sources & evidence

ORD record
ord-adda741acd6c4f4b845bc6def37e7cfe
Source dataset
uspto-grants-1981_03
Patent number
US04254267

Linked notes

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