1-Dodecanol → 5-Dodecyloxy-2-furoic acid

HRID 2420264Notes

Reaction equation

HRID 2420264 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([OH:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[H-].[Na+]>N1C=CC=CC=1>[CH2:10]([O:22][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][CH3:21]

Participants

5

Reactant 3

HCID 81931-DodecanolHCID 24758Sodium hydrideHCID 685115-Bromo-2-furanecarboxylic acid

Product 1

HCID 123615075-Dodecyloxy-2-furoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 30.0 g (0.157 mole) of 5-bromofuroic acid, 29.4 g (0.157 mole) of dodecanol and 500 ml of pyridine is flushed with nitrogen and stirred at room temperature after which 7.55 g (0.314 mole) of sodium hydride is added. The mixture is heated to 100° C for 20 hours, then refluxed 1 hour after which 2.0 g of cuprous chloride is added. The mixture is refluxed with stirring under nitrogen for 20 hours, then poured into an ice-water-hydrochloric acid mixture with stirring and filtered. The resulting oily precipitate is extracted into ether, washed with 5% hydrochloric acid solution, water and salt water, dried over sodium sulfate, filtered, and evaporated on a steam bath replacing the ether with hexane. The solid obtained is recrystallized from methanol to give 5-dodecyloxy-2-furoic acid, M.P. 122°-123° C.

Workup

  1. customis flushed with nitrogen
  2. additionis added
  3. additionis added
  4. temperatureThe mixture is refluxed
  5. stirringwith stirring
  6. filtrationfiltered
  7. extractionThe resulting oily precipitate is extracted into ether
  8. washwashed with 5% hydrochloric acid solution, water and salt water
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated on a steam bath
  12. customThe solid obtained
  13. customis recrystallized from methanol

Sources & evidence

ORD record
ord-91f707f3e67443bab9485d5a78a3fc60
Source dataset
uspto-grants-1978_08
Patent number
US04110351

Reaction notes

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