Citric Acid → 2-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuran

HRID 1534199ノート

反応式

HRID 1534199 の反応式
[OH:1][C:2]1[C:7]2[C:8]([CH3:21])=[C:9]([C:11](=O)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:22][CH2:23][CH3:24].[OH-].[K+].NN.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C(O)CO>[OH:1][C:2]1[C:7]2[C:8]([CH3:21])=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:22][CH2:23][CH3:24]

参加物

7

反応物 4

HCID 311Citric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 145797604-Hydroxy-2-(4-methoxybenzoyl)-3-methyl-5-propylbenzofuran

生成物 1

HCID 145708892-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuran収率 58.6%

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 962Water溶媒

実験手順

A mixture of 4-hydroxy-2-(4-methoxybenzoyl)-3-methyl-5-propylbenzofuran (7.2 g; 22 mmoles), potassium hydroxide pellets (8.7 g; 155 mmoles), ethylene glycol (100 ml) and 99% hydrazine (3.0 ml) was heated with stirring and maintaining the internal temperature between 130° C. and 150° C. for 4 hours. The internal temperature was permitted to rise to 175° C. for 1 hour and excess water was always allowed to escape. The mixture was cooled and poured into excess 20% citric acid solution. The mixture was extracted with ether, washed with water, dried (Na2SO4), filtered, concentrated, and chromatographed to give 4 grams of the title compound.

後処理

  1. temperaturewas heated
  2. temperaturemaintaining the internal temperature between 130° C. and 150° C. for 4 hours
  3. temperatureThe mixture was cooled
  4. extractionThe mixture was extracted with ether
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed

出典と根拠

ORDレコード
ord-d172ec0f45d946e38584b438c4f087b9
出典データセット
uspto-grants-1992_02
特許番号
US05087638

反応ノート

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