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

HRID 1708724ノート

反応式

HRID 1708724 の反応式
[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

参加物

8

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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 in 100 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.

後処理

  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

出典と根拠

ORDレコード
ord-066e1885604042a4a0865a189c3c1003
出典データセット
uspto-grants-1994_10
特許番号
US05359098

反応ノート

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