1-Decanol → HCID 12361506, compound

HRID 614759Notes

Reaction equation

HRID 614759 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([OH:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].CC(N(C)C)=O.[H-].[Na+]>C(O)(=O)C>[CH2:10]([O:20][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][CH3:19]

Participants

6

Reactant 4

HCID 81741-DecanolHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 685115-Bromo-2-furanecarboxylic acid

Product 1

HCID 12361506HCID 12361506, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 30.0 g (0.157 mole) of 5-bromofuroic acid, 75.4 g (0.471 mole) of decanol and 1000 ml of dried dimethyl acetamide is stirred at room temperature after which 15.0 g (0.628 mole) of sodium hydride is added. The mixture is refluxed with stirring for 42 hours after which the mixture is poured into a water-ice mixture, acidified with acetic acid and extracted with ether. The ether layer is washed several times with water and salt water, then dried over sodium sulfate, filtered and evaporated on a steam bath replacing the ether with hexane and allowing the mixture to crystallize. The solid obtained is recrystallized from methanol to give 5-decyloxy-2-furoic acid, M.P. 124°-126° C.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed
  3. extractionextracted with ether
  4. washThe ether layer is washed several times with water and salt water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated on a steam bath
  8. customto crystallize
  9. customThe solid obtained
  10. customis recrystallized from methanol

Sources & evidence

ORD record
ord-d7533df818d2460fbba19df4b455f3ac
Source dataset
uspto-grants-1979_03
Patent number
US04146623

Reaction notes

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