4-Hydroxybenzaldehyde → 4-(4-[6-Acryloyloxyhexyloxy]phenylcarbonyloxy)benzaldehyde

HRID 233418ノート

反応式

HRID 233418 の反応式
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].O[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.O>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][C:23]2[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=2)=[O:18])=[CH:20][CH:21]=1)(=[O:4])[CH:2]=[CH2:3]

参加物

6

反応物 3

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

生成物 1

HCID 233558004-(4-[6-Acryloyloxyhexyloxy]phenylcarbonyloxy)benzaldehyde収率 92.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

0.6 g of N,N'-dicyclodicyclohexylcarbodiimide is added at room temperature while stirring to a solution of 1.0 g of 4-[6-acryloyloxyhexyloxy]benzoic acid, 0.3 g of 4-hydroxybenzaldehyde and 0.04 g of 4-dimethylaminopyridine in 20 ml of dichloromethane. The reaction mixture is stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of dichloromethane each time. The combined organic phases are washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and the filtrate is subsequently concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 1:1) and two-fold recrystallization from ethanol of the fractions which are pure according to thin-layer chromatography gives 0.9 g of 4-(4-[6-acryloyloxyhexyloxy]phenylcarbonyloxy)benzaldehyde.

後処理

  1. addition0.6 g of N,N'-dicyclodicyclohexylcarbodiimide is added at room temperature
  2. extractionextracted three times with 50 ml of dichloromethane each time
  3. washThe combined organic phases are washed twice with 100 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is subsequently concentrated
  7. customChromatographic purification of the residue on silica gel
  8. customwith hexane/ethyl acetate (vol. 1:1) and two-fold recrystallization from ethanol of the fractions which

出典と根拠

ORDレコード
ord-953181295d8246269c1c0e0eba1ecf74
出典データセット
uspto-grants-1997_01
特許番号
US05593617

反応ノート

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