Water → HCID 54448030, compound

HRID 1981367Notes

Reaction equation

HRID 1981367 reaction equation
C([O:3][C:4](=[O:19])[CH:5](Br)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])C.[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([OH:29])=[CH:23][C:22]=2[O:21]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([O:29][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:4]([OH:3])=[O:19])=[CH:23][C:22]=2[O:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 68289SesamolHCID 85791Tetradecanoic acid, 2-bromo-, ethyl ester

Product 1

HCID 54448030HCID 54448030, compoundYield 109.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

33.5 g of 2-bromotetradecanoic acid ethyl ester and 13.8 g of 3,4-methylenedioxyphenol were dissolved in 100 ml of dimethylformamide, to which was added 13.8 g of anhydrous potassium carbonate while introducing a nitrogen gas and the mixture was stirred at 90° C. for 6 hours. The reaction solution was poured into 300 ml of cold water and extracted with 300 ml of ethyl acetate. The ethyl acetate layer was washed with 300 ml of water and the ethyl acetate was distilled off under reduced pressure. To the residue was added 120 ml of a 10% methanol solution of potassium hydroxide and the mixture was refluxed for 30 minutes. The reaction mixture was poured into 300 ml of a cold 7% aqueous hydrochloric acid solution and extracted with 300 ml of ethyl acetate. The ethyl acetate layer was washed with 300 ml of water and dried with anhydrous sodium sulfate. After removing the sodium sulfate by filtration, the ethyl acetate was distilled off under reduced pressure and to the resulting residue was added 70 ml of acetonitrile to crystallize. The crystals thus deposited were collected by filtration to obtain 40 g of 2-(3,4-methylenedioxyphenoxy)tetradecanoic acid having a melting point of 70° to 72° C.

Workup

  1. additionwhile introducing a nitrogen gas
  2. extractionextracted with 300 ml of ethyl acetate
  3. washThe ethyl acetate layer was washed with 300 ml of water
  4. distillationthe ethyl acetate was distilled off under reduced pressure
  5. additionTo the residue was added 120 ml of a 10% methanol solution of potassium hydroxide
  6. temperaturethe mixture was refluxed for 30 minutes
  7. additionThe reaction mixture was poured into 300 ml of a cold 7% aqueous hydrochloric acid solution
  8. extractionextracted with 300 ml of ethyl acetate
  9. washThe ethyl acetate layer was washed with 300 ml of water
  10. dry with materialdried with anhydrous sodium sulfate
  11. customAfter removing the sodium sulfate
  12. filtrationby filtration
  13. distillationthe ethyl acetate was distilled off under reduced pressure and to the resulting residue
  14. additionwas added 70 ml of acetonitrile
  15. customto crystallize
  16. filtrationThe crystals thus deposited were collected by filtration

Sources & evidence

ORD record
ord-592e8242d2e04a918f367ded699d51ea
Source dataset
uspto-grants-1985_04
Patent number
US04514490

Reaction notes

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