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

HRID 889478Notes

Reaction equation

HRID 889478 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c7515423828d435997a20d59a2e8f12c
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

Loading…