Benzaldehyde → 6-(6-chlorohexoxy)-3-hydroxy-4H-1-benzopyran-4-one

HRID 1197977Notes

Reaction equation

HRID 1197977 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8]C1C=CC(O)=C(C(=O)C)C=1.[CH:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-:27].[Na+].OO.Cl.[CH2:32]([OH:34])[CH3:33]>O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:24]1[CH:23]=[CH:22][C:21]2[O:34][CH:32]=[C:33]([OH:27])[C:19](=[O:26])[C:20]=2[CH:25]=1

Participants

8

Reactant 6

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 149830945'-(6-Chlorohexoxy)-2'-hydroxyacetophenone

Product 1

HCID 189596836-(6-chlorohexoxy)-3-hydroxy-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 5'-(6-chlorohexoxy)-2'-hydroxyacetophenone (32 g) and benzaldehyde (12 g) was dissolved in 250 mL of ethanol. A solution of 24 g of sodium hydroxide dissolved in 40 mL of water was added. This mixture was allowed to stand at room temperature for 6 hours. A solution of 8 g of sodium hydroxide dissolved in 40 mL of water was added, the solution was cooled to 15°-20° C., and then 20 mL of hydrogen peroxide (30% solution) was added and the solution was allowed to warm to room temperature and was stirred overnight. Then the solution's pH was adjusted to 3 using hydrochloric acid. The yellow precipitate was collected by vacuum filtration and washed with water, ethanol, and ether to give 16 g of 6-(6-chlorohexoxy)-3-hydroxy-4H- 1-benzopyran-4-one. Next, 10 g of 6-(6-chlorohexoxy)-3-hydroxy-4H-1-benzopyran-4-one was dissolved in100 mL of tetrahydrofuran. Then 800 mg of sodium hydride was added followed by 8.3 mL of methyl iodide and the resulting solution was stirred at room temperature for 48 hours. The reaction was poured into water and extracted with ethyl acetate. The combined organic layers were washed with water and then with brine. After drying over sodium sulfate, the solvent was removed to give 8 g of 6-(6- chlorohexoxy)-3-methoxy-4H-1-benzopyran-4-one.

Workup

  1. additionwas added
  2. additionwas added
  3. temperaturethe solution was cooled to 15°-20° C.
  4. filtrationThe yellow precipitate was collected by vacuum filtration
  5. washwashed with water, ethanol, and ether

Sources & evidence

ORD record
ord-706c518472d44a0684244723f5a32530
Source dataset
uspto-grants-1994_01
Patent number
US05278174

Reaction notes

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