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

HRID 233418

반응식

HRID 233418 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-953181295d8246269c1c0e0eba1ecf74
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593617

연결된 노트

불러오는 중…