2-Thiocresol → HCID 21162536, compound

HRID 894238Notes

Reaction equation

HRID 894238 reaction equation
[C:1]1([CH3:8])[C:2]([SH:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.Br[C:10]1[O:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=1>CN(C)C=O>[CH3:8][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:10]1[O:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=1

Participants

4

Reactant 2

HCID 87122-ThiocresolHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 21162536HCID 21162536, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
175 °C

Procedure

In an open flask cuprous oxide (2.25 g., 15.7 mmoles) and o-toluenethiol (3.89 g., 31.4 mmoles) were combined in 40 ml. of dimethylformamide and heated in a 150° C. oil bath until a thick yellow mixture formed. The mixture was cooled slightly and 5-bromofuran-3-carboxylic acid [3.0 g., 15.7 mmoles; Gilman and Burtner, J. Am. Chem. Soc. 55, 2903 (1933)] in 40 ml. of dimethylformamide added. The mixture was heated in a 175° C. oil bath for approximately 16 hours. The reaction mixture was cooled, solids removed by filtration, the filtrate diluted with 500 ml. of water, acidified with 6 N hydrochloric acid and product extracted into three portions of ethyl acetate. The ethyl acetate extracts were combined, evaporated to an oil, the oil taken up in 1 N sodium hydroxide, the basic solution washed with ether, cooled, reacidified and product (650 mg.) recovered by filtration. Recrystallization from methanol/water gave purified 5-(2-methylphenylthio)furan-3-carboxylic acid (485 mg., m.p. 148°-150° C., m/e 234).

Workup

  1. customformed
  2. temperatureThe mixture was cooled slightly
  3. temperatureThe reaction mixture was cooled
  4. customsolids removed by filtration
  5. additionthe filtrate diluted with 500 ml
  6. extractionextracted into three portions of ethyl acetate
  7. customevaporated to an oil
  8. washthe basic solution washed with ether
  9. temperaturecooled
  10. filtrationproduct (650 mg.) recovered by filtration
  11. customRecrystallization from methanol/water
  12. customgave
  13. custompurified 5-(2-methylphenylthio)furan-3-carboxylic acid (485 mg., m.p. 148°-150° C., m/e 234)

Sources & evidence

ORD record
ord-717d43d19e5d48049127d4da1c0dcb5f
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

Loading…