2,4-Dihydroxybenzaldehyde → HCID 56692933、化合物

HRID 2045736

反応式

HRID 2045736 の反応式
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].O[C:17]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:18]=1[CH:19]=O>C(OC(=O)C)(=O)C.C(N(CC)CC)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[C:13](=[O:15])[O:14][C:21]3[C:18]([CH:19]=2)=[CH:17][CH:24]=[C:23]([OH:25])[CH:22]=3)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 2

HCID 72132,4-DihydroxybenzaldehydeHCID 78304Acetic acid, (p-butoxyphenyl)-

生成物 1

HCID 56692933HCID 56692933、化合物

試薬・触媒・溶媒 2

HCID 7918Acetic Anhydride溶媒HCID 8471Triethylamine溶媒

実験手順

89.5 g (0.43 mol) of 4-butoxyphenylacetic acid (prepared by the method of McElvain, Carney; J. Am. Chem. Soc. 1946 (68), 2592-2599) and 30.0 g (0.22 mol) of 2,4-dihydroxybenzaldehyde are heated at 120° C. for 5 h in 100 ml of acetic anhydride and 120 ml of triethylamine. The still-hot solution is subsequently added to 3 l of ice-water, and the precipitated product is filtered off with suction and suspended in 1 l of water and 1.4 l of ethanol. After dropwise addition of 190 ml of conc. sulfuric acid, the batch is heated under reflux for 4 h and added to 3 l of water, and the precipitated product is filtered off with suction. The crude product is filtered through silica gel with hot toluene/ethyl acetate (1:1), the solvent is evaporated in vacuo, and the residue is recrystallised from toluene, giving 3-(4-butoxyphenyl)-7-hydroxychromen-2-one as colourless crystals.

後処理

  1. filtrationthe precipitated product is filtered off with suction
  2. additionAfter dropwise addition of 190 ml of conc. sulfuric acid
  3. temperaturethe batch is heated
  4. temperatureunder reflux for 4 h
  5. additionadded to 3 l of water
  6. filtrationthe precipitated product is filtered off with suction
  7. filtrationThe crude product is filtered through silica gel with hot toluene/ethyl acetate (1:1)
  8. customthe solvent is evaporated in vacuo
  9. customthe residue is recrystallised from toluene

出典と根拠

ORDレコード
ord-3c5d251a63444791b379bee585abec58
出典データセット
uspto-grants-2013_11
特許番号
US08592007B2

関連ノート

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