Acetone → Diethyl 1,4-bis(propyloxy)-2,3-naphthalenedicarboxylate

HRID 889478노트

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HRID 889478 반응식
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH3:32].[CH3:33][C:34]([CH3:36])=O>C1(C)C=CC=CC=1>[CH2:30]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:33][CH2:34][CH3:36])=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:31][CH3:32]

참가 물질

6

반응물 4

HCID 180AcetoneHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 431092,3-Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate

생성물 1

HCID 58017588Diethyl 1,4-bis(propyloxy)-2,3-naphthalenedicarboxylate

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
60 °C

실험 절차

Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate* (11 g, 36.1 mmol) was dissolved in acetone (180 ml) and potassium carbonate (24.9 g, 180.5 mmol) added and stirred. 1-Bromopropane (13.1 ml, 144.4 mmol) was added and the reaction mixture was heated at reflux (60° C.) overnight under argon. The reaction was cooled to room temperature and the inorganic solid filtered off. The solvent was evaporated to give an orange brown oil. The residue was taken up in toluene and washed with 5% potassium hydroxide solution, brine and dried over magnesium sulphate. Solvent was removed under vacuum to give a brown oil which was purified by chromatography on silica gel eluting with, 10% ethyl acetate in hexane. The clean fractions were evaporated to give the title compound as yellow oil (11.45 g, 29.5 mmol).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationthe inorganic solid filtered off
  4. customThe solvent was evaporated
  5. customto give an orange brown oil
  6. washwashed with 5% potassium hydroxide solution, brine
  7. dry with materialdried over magnesium sulphate
  8. customSolvent was removed under vacuum
  9. customto give a brown oil which
  10. customwas purified by chromatography on silica gel eluting with, 10% ethyl acetate in hexane
  11. customThe clean fractions were evaporated

출처 및 근거

ORD 기록
ord-c7515423828d435997a20d59a2e8f12c
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252833B2

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