Potassium Carbonate → Methyl 3,5-bis(docosyloxy)benzoate

HRID 573961

Reaction equation

HRID 573961 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][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][CH2:27][CH2:28][CH3:29].[OH:30][C:31]1[CH:32]=[C:33]([CH:38]=[C:39]([OH:41])[CH:40]=1)[C:34]([O:36][CH3:37])=[O:35]>CN(C)C=O>[CH2:8]([O:30][C:31]1[CH:32]=[C:33]([CH:38]=[C:39]([O:41][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])[CH:40]=1)[C:34]([O:36][CH3:37])=[O:35])[CH2:9][CH2:10][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][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75076Methyl 3,5-DihydroxybenzoateHCID 813551-Bromodocosane

Product 1

HCID 66651984Methyl 3,5-bis(docosyloxy)benzoateYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Potassium carbonate (19.9 g, 144 mmol) was suspended in dehydrating N,N-dimethylformamide (200 mL), 1-bromodocosane (15.6 g, 46.7 mmol) and methyl (3,5-dihydroxy)benzoate (3.60 g, 21.4 mmol) were added, and the mixture was stirred at 90° C. overnight. After completion of the reaction, the reaction mixture was poured into purified water (800 mL), the mixture was stirred for 1 hr, and the precipitated solid was collected by filtration. The obtained solid was dissolved again in dichloromethane (800 mL), and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and acetone was added again to precipitate a solid. The solid was collected by filtration and slurry-washed in methanol. After filtration, the obtained solid was dried under reduced pressure to give the title compound (13.9 g, 96.5%) as a white solid.

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. additionthe reaction mixture was poured
  4. custominto purified water (800 mL)
  5. stirringthe mixture was stirred for 1 hr
  6. filtrationthe precipitated solid was collected by filtration
  7. dissolutionThe obtained solid was dissolved again in dichloromethane (800 mL)
  8. filtrationthe insoluble material was filtered off
  9. concentrationThe filtrate was concentrated under reduced pressure, and acetone
  10. additionwas added again
  11. customto precipitate a solid
  12. filtrationThe solid was collected by filtration
  13. washslurry-washed in methanol
  14. filtrationAfter filtration
  15. customthe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-c82dc7d4c875440ebb54abfe835d20f0
Source dataset
uspto-grants-2015_05
Patent number
US09029528B2

Linked notes

Loading…