1-Tetradecanol → 5-(Tetradecyloxy)-2-furoic acid

HRID 649221Notes

Reaction equation

HRID 649221 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([OH: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].CC(C)([O-])C.[K+].CC(N(C)C)=O>C(O)(C)(C)C>[CH2:10]([O: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 82091-TetradecanolHCID 31374DimethylacetamideHCID 685115-Bromo-2-furanecarboxylic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 1151755-(Tetradecyloxy)-2-furoic acidYield 38.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 125.0 g (0.652 mole) of 5-bromo-2-furoic acid, 210.0 g (0.978 mole) of 1-tetradecanol, 183.0 g (1.630 mole) of potassium tert-butoxide and 2500 ml of dimethylacetamide is heated with stirring. The tert-butanol formed in the reaction is allowed to distill off, then the mixture is heated to reflux with stirring for 48 hours. To the cooled mixture is added 6 liters of ice water, and the mixture is acidified with malonic acid. The resulting precipitate is collected, dried and recrystallized twice from methanol to give 82.0 g (29%) of 5-tetradecyloxy-2-furoic acid, M.P. 112°-115° C. (dec.).

Workup

  1. temperatureis heated
  2. distillationto distill off
  3. temperaturethe mixture is heated
  4. temperatureto reflux
  5. stirringwith stirring for 48 hours
  6. additionTo the cooled mixture is added 6 liters of ice water
  7. customThe resulting precipitate is collected
  8. customdried
  9. customrecrystallized twice from methanol

Sources & evidence

ORD record
ord-80f1a65424a54e29aa7cd1f111c58f66
Source dataset
uspto-grants-1988_04
Patent number
US04738984

Reaction notes

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