Diglyme → HCID 12361513, compound

HRID 614763Notes

Reaction equation

HRID 614763 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][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].COCCOCCOC.[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][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 8150DiglymeHCID 8221Stearyl AlcoholHCID 24758Sodium hydrideHCID 685115-Bromo-2-furanecarboxylic acid

Product 1

HCID 12361513HCID 12361513, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 30.0 g (0.157 mole) of 5-bromofuroic acid, 64.0 g (0.236 mole) of octadecanol and 500 ml of bis(2-methoxyethyl)ether is stirred at room temperature under nitrogen after which 9.45 g (0.393 mole) of sodium hydride is added. The mixture is refluxed about 22 hours, allowed to cool and 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, and filtered. The solvent is evaporated off replacing the ether with hexane. Upon cooling to room temperature a solid forms which is recrystallized from methanol to give 5-octadecyloxy-2-furoic acid, M.P. 117°-118° C.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed about 22 hours
  3. temperatureto cool
  4. extractionextracted with ether
  5. washThe ether layer is washed with water and salt water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent is evaporated off
  9. customis recrystallized from methanol

Sources & evidence

ORD record
ord-85568150f0684ea1b4c2f179fc083e31
Source dataset
uspto-grants-1979_03
Patent number
US04146623

Reaction notes

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