Potassium Chloride → Methyl-3,5-didecoxybenzoate

HRID 2055751Notes

Reaction equation

HRID 2055751 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Cl-].[K+].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[C:21]([OH:23])[CH:20]=[C:19]([OH:24])[CH:18]=1>CN(C)C=O>[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:18]=[C:19]([O:24][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:20]=[C:21]([O:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:22]=1

Participants

5

Reactant 3

HCID 4873Potassium ChlorideHCID 81731-BromodecaneHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 10343663Methyl-3,5-didecoxybenzoateYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 1 L round bottom flask (RBF), while stirring with a magnetic stir bar, 1-bromodecane (54.3 mL, 0.262 mol), dimethylformamide (DMF) (200 mL), and potassium chloride (49.3 g, 0.357 mol) were added. Methyl-3,5-dihydroxybenzoate (20.0 g, 0.119 mol) was dissolved in DMF (100 mL) and the solution was added to the 1 L RBF. The solution gradually changed from an opaque pale yellow to an opaque light grey. The reaction vessel was sealed with a rubber septum and was stirred overnight. After stirring for approximately 20 hours, the contents of the RBF changed to a dark grey color and solidified. The RBF was gently heated with a heat gun until the contents liquefied. After cooling to just above room temperature, the contents of the RBF were transferred into a 2 L Erlenmeyer Flask that contained 1 L of 30/70 ice/distilled H2O mixture. A white precipitate formed on contact with H2O. Vacuum filtration was used to isolate the precipitate. The white precipitate was recrystallized from absolute ethanol (800 mL) and allowed to cool slowly overnight. The contents were then vacuum filtered yielding fine bright white fibrous crystals. The filtrate was concentrated under reduced pressure to approximately 300 mL. The concentrated filtrate was warmed and then left in refrigerator for approximately 18 hours. A second crop of fine bright white fibrous crystals was isolated from the solution upon vacuum filtration. The remaining pale yellow colored filtrate was discarded. This gave a total of 51.5 g yield or a 96.5% yield of the derivative. The NMR characterization data for this derivative is as follows. 1NMR (300 MHz, CDCl3): 0.88 (t, J=6.6, 6H, CH2CH3), 1.27-1.44 (m, 28H, CH2(CH2)7), 1.80 (p, J=6.9, 4H, OCH2CH2), 3.89 (s, 3H, OCH3), 3.93 (t, J=6.6, 4H, OCH2CH2), 6.63 (t, J=2.2, 1H, ArH), 7.15 (d, J=2.5, 2H, ArH). 13C NMR (75 MHz, CDCl3): 14.22, 22.78, 26.10, 29.26, 29.42, 29.45, 29.65, 31.99, 52.27, 68.37, 77.31, 106.61, 107.65, 131.86, 160.21, 167.08.

Workup

  1. additionthe solution was added to the 1 L RBF
  2. customThe reaction vessel was sealed with a rubber septum
  3. stirringwas stirred overnight
  4. stirringAfter stirring for approximately 20 hours
  5. temperatureThe RBF was gently heated with a heat gun until the contents
  6. temperatureAfter cooling to just above room temperature
  7. distillationdistilled H2O mixture
  8. customA white precipitate formed on contact with H2O
  9. filtrationVacuum filtration
  10. customto isolate the precipitate
  11. customThe white precipitate was recrystallized from absolute ethanol (800 mL)
  12. temperatureto cool slowly overnight
  13. filtrationvacuum filtered
  14. customyielding fine bright white fibrous crystals
  15. concentrationThe filtrate was concentrated under reduced pressure to approximately 300 mL
  16. temperatureThe concentrated filtrate was warmed
  17. customA second crop of fine bright white fibrous crystals was isolated from the solution upon vacuum filtration
  18. customThis gave a total of 51.5 g
  19. customyield

Sources & evidence

ORD record
ord-620d4cd98db14da39c50f8f59a4fa330
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

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