Potassium Carbonate → 6-(Pentyloxy)-2h-3-chromenecarbaldehyde

HRID 428200Notes

Reaction equation

HRID 428200 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][C:6]([CH:12]=[O:13])=[CH:5]2.I[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][C:6]([CH:12]=[O:13])=[CH:5]2)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 123351-IodopentaneHCID 47708156-Hydroxychromene-3-carboxaldehyde

Product 1

HCID 181774176-(Pentyloxy)-2h-3-chromenecarbaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2 g (11.4 mmol) of the hydroxyaldehyde obtained in Step A and also 2.7 g (13.6 mmol) of iodopentane are added to a suspension of 1.9 g (13.6 mmol) of potassium carbonate in 50 ml of anhydrous acetone; the medium is then heated at reflux. After one hour, 1.2 g of potassium carbonate are added to the solution, and that operation is then re-started after one hour. At the end of 12 hours of heating at reflux, the solution is allowed to cool, the salts are filtered off over Celite and the solvent is then evaporated in vacuo. Chromatography on a silica column (eluant:petroleum ether/ethyl acetate 90/10) yields the title aldehyde in the form of a yellow syrup.

Workup

  1. temperaturethe medium is then heated
  2. temperatureat reflux
  3. waitre-started after one hour
  4. temperatureAt the end of 12 hours of heating
  5. temperatureat reflux
  6. temperatureto cool
  7. filtrationthe salts are filtered off over Celite
  8. customthe solvent is then evaporated in vacuo

Sources & evidence

ORD record
ord-d0caf56b8f0742369c6e5203a524b0df
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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