Dimethylformamide → HCID 58788081, compound

HRID 2055760Notes

Reaction equation

HRID 2055760 reaction equation
CN([CH:4]=[O:5])C.O[C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([OH:17])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>O>[CH2:25]([O:17][C:15]1[CH:14]=[C:9]([CH:8]=[C:7]([O:5][CH2:4][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 58788081HCID 58788081, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 1 L RBF containing a stir bar and DMF (100 mL); methyl 3,5-dihydroxylbenzoate (20 g, 0.1190 M), potassium carbonate (49.34 g, 0.3570 M), 1-bromododecane (57.2 mL, 0.2380 M) and DMF (100 mL) were added. The reaction mixture was covered with a septum and stirred overnight. By the end of the reaction period (15 hours), the reaction mixture had turned from a pale yellow suspension to a solid dark green suspension. Heat was applied to the RBF until the reaction mixture became fluid. The dark green mixture was then added to 1 L of distilled water and ice, and copious precipitation occurred immediately. The precipitate was isolated by vacuum filtration. The precipitate was recrystallized from hot ethanol (1 L). To increase the product yield, the solution was left to stand at room temperature overnight. The crystals were vacuum filtered and the crystals air-dried yielding 58.5 g or 96.7%. The NMR characterization data for the derivative is as follows. 1H NMR (300 MHz, CDCl3): 0.87 (t, J=6.6, 6H, CH2CH3), 1.15-1.6 (m, 28H, CH2(CH2)6), 1.76 (p, J=8.0, 8H, OCH2CH2), 3.89 (s, 3H, OCH3), 3.95 (t, J=6.6, 4H, OCH2CH2), 6.62 (t, J=2.5, 1H, ArH), 7.15 (d, J=2.5, 2H, ArH).

Workup

  1. additionIn a 1 L RBF containing a stir bar
  2. customBy the end of the reaction period (15 hours)
  3. temperatureHeat
  4. customThe precipitate was isolated by vacuum filtration
  5. customThe precipitate was recrystallized from hot ethanol (1 L)
  6. temperatureTo increase the product
  7. customyield
  8. waitthe solution was left
  9. waitto stand at room temperature overnight
  10. filtrationfiltered
  11. customthe crystals air-dried
  12. customyielding 58.5 g or 96.7%

Sources & evidence

ORD record
ord-c5404a0b178f43f1843248f06cdbb96c
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

Loading…