Hydrochloric Acid → HCID 69823554, compound

HRID 342784Notes

Reaction equation

HRID 342784 reaction equation
[C:1]([C:5]1[C:14]2[C:9](=[C:10]([CH2:16][CH2:17][CH3:18])[C:11]([OH:15])=[CH:12][CH:13]=2)O[C:7](=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:20][CH2:21][CH2:22][CH2:23]Br.[C:25](=[O:28])([O-:27])[O-].[K+].[K+].Cl.CC(=[O:36])CC>C(OCC)(=O)C>[Br:20][CH2:21][CH2:22][CH2:23][O:15][C:11]1([OH:36])[C:10]([CH2:16][CH2:17][CH3:18])=[C:9]2[C:14](=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]([CH3:7])[C:25](=[O:28])[O:27]2)[CH:13]=[CH:12]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6569Methyl Ethyl KetoneHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 53691952HCID 53691952, compound

Product 1

HCID 69823554HCID 69823554, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-tert-butyl-7-hydroxy-8-propylcoumarin (380 mg), 1,3-dibromopropane (0.45 ml) and potassium carbonate (240 mg) in 2-butanone (15 ml) was refluxed for five hours. The mixture was partioned between 0.2N HCl and ethyl acetate, dried over magnesium sulfate and concentrated. Column Chromatography (silica gel 60, 50% methylene chloride in hexane) gave the title compound.

Workup

  1. dry with materialdried over magnesium sulfate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-dd74662a6247435ab67e498a2b004201
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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