Potassium Carbonate → HCID 19847946, compound

HRID 2351071Notes

Reaction equation

HRID 2351071 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:24]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 127441-BromoundecaneHCID 24758Sodium hydrideHCID 728635-Bromosalicylaldehyde

Product 1

HCID 19847946HCID 19847946, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-Bromosalicylaldehyde (1.51 g, 7.5 mm) was dissolved in dry DMF and treated with sodium hydride (0.4 g, 8.3 mm, 50% dispersion). After stirring for 20 minutes, a solution of 1-bromo-undecane in DMF was added dropwise. The reaction was heated to 50°-65° C. overnight with stirring. The reaction was then poured into ice water, the pH was adjusted to 8.0 with K2CO3 and the mixture was extracted with diethylether. The organic extracts were washed with water, dried over MgSO4 and filtered. The solvent was evaporated to yield an oil which solidifies upon standing.

Workup

  1. temperatureThe reaction was heated to 50°-65° C. overnight
  2. stirringwith stirring
  3. extractionthe mixture was extracted with diethylether
  4. washThe organic extracts were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customto yield an oil which

Sources & evidence

ORD record
ord-a02549e1ea464bf09b151f982d818363
Source dataset
uspto-grants-1989_10
Patent number
US04871771

Reaction notes

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