tert-Butanol → HCID 54447207, compound

HRID 649224Notes

Reaction equation

HRID 649224 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([OH:26])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH:21]=[CH:22][CH2:23][CH:24]=[CH2:25].CC(C)([O-])C.[K+].C(O)(C)(C)C>C1(C)C=CC=CC=1>[CH2:10]([O:26][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][CH:21]=[CH:22][CH2:23][CH:24]=[CH2:25]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 685115-Bromo-2-furanecarboxylic acidHCID 23665647Potassium tert-butoxideHCID 54040177HCID 54040177, compound

Product 1

HCID 54447207HCID 54447207, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 57.0 g (0.300 mole) of 5-bromo-2-furoic acid, 119.0 g (0.450 mole) of 9,12,15-hexadecatrienol, and 84 g (0.750 mole) of potassium tert-butoxide in dry toluene is stirred with heating. The tert-butanol formed in the reaction is allowed to distill off, and the mixture is refluxed at 110° C. with stirring for 48 hours. The mixture is allowed to cool, then is acidified with acetic acid and diluted with ice water. The toluene organic layer is separated, washed with water, then extracted three times with 5% sodium bicarbonate solution. The combined aqueous extracts are cooled and acidified with 10% HCl solution to give 5-(9,12,15-hexadecatrienyloxy)-2-furoic acid.

Workup

  1. temperaturewith heating
  2. distillationto distill off
  3. stirringwith stirring for 48 hours
  4. temperatureto cool
  5. additiondiluted with ice water
  6. customThe toluene organic layer is separated
  7. washwashed with water
  8. extractionextracted three times with 5% sodium bicarbonate solution
  9. temperatureThe combined aqueous extracts are cooled

Sources & evidence

ORD record
ord-db3123ccdb0949038373755f88185f60
Source dataset
uspto-grants-1988_04
Patent number
US04738984

Reaction notes

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