Dimethylformamide → HCID 70362851, compound

HRID 614760Notes

Reaction equation

HRID 614760 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([OH:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].CN(C)C=O.[H-].[Na+]>C(O)(=O)C>[CH2:10]([O:28][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]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 685115-Bromo-2-furanecarboxylic acidHCID 5284499Oleyl Alcohol

Product 1

HCID 70362851HCID 70362851, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 30.0 g (0.157 mole) of 5-bromofuroic acid, 43.7 g (0.157 mole) of oleylalcohol and 500 ml of dried dimethylformamide 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 stirred at room temperature for an hour then heated to reflux. The mixture is refluxed for 92 hours after which the mixture is poured into an ice-water mixture, acidified with acetic acid and extracted with ether. The ether layer is washed with water and salt water, dried over sodium sulfate, filtered and evaporated replacing the ether with hexane. Upon cooling a solid is formed which is recrystallized from methanol to give 5-(cis-9-octadecenyloxy)-2-furoic acid, M.P. 93°-96° C.

Workup

  1. customis flushed with nitrogen
  2. additionis added
  3. temperaturethen heated to reflux
  4. temperatureThe mixture is refluxed for 92 hours after which the mixture
  5. extractionextracted with ether
  6. washThe ether layer is washed with water and salt water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. temperatureUpon cooling a solid
  11. customis formed which
  12. customis recrystallized from methanol

Sources & evidence

ORD record
ord-d1c8a7482b7248a690fc396502d8baeb
Source dataset
uspto-grants-1979_03
Patent number
US04146623

Reaction notes

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