Acetic Acid → 5-Tetradecylthio-2-furoic acid

HRID 614764Notes

Reaction equation

HRID 614764 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([SH:24])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[H-].[Na+].C(O)(=O)C>CN(C)C=O>[CH2:10]([S:24][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 646771-TetradecanethiolHCID 685115-Bromo-2-furanecarboxylic acid

Product 1

HCID 123615095-Tetradecylthio-2-furoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 20.1 g (0.011 mole) of 5-bromofuroic acid, 24.2 g (0.011 mole) of tetradecanethiol in 800 ml of dimethylformamide and 8.5 g (0.021 mole) of sodium hydride is heated on a steam bath overnight then refluxed for one-half hour. The mixture is then cooled, acidified with acetic acid and extracted with ether-water. The ether layer is washed with water and salt water, dried over sodium sulfate and filtered. The filtrate is evaporated to dryness, and the remaining solid is recrystallized from hexane and from methanol to give 5-tetradecylthio-2-furoic acid, M.P. 84°-86° C.

Workup

  1. temperatureis heated on a steam bath overnight
  2. temperaturethen refluxed for one-half hour
  3. temperatureThe mixture is then cooled
  4. extractionextracted with ether-water
  5. washThe ether layer is washed with water and salt water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate is evaporated to dryness
  9. customthe remaining solid is recrystallized from hexane and from methanol

Sources & evidence

ORD record
ord-447fadad63b548369a3d56bd513105b7
Source dataset
uspto-grants-1979_03
Patent number
US04146623

Reaction notes

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