Hydrochloric Acid → 1-(6-Methoxy-2-naphthyl)-4-phenylbutane-1,4-dione

HRID 456811Notes

Reaction equation

HRID 456811 reaction equation
[C:1]([CH:9]([CH2:15][C:16]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH3:29])[CH:24]=2)[CH:19]=1)=[O:17])C(OCC)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1>[CH3:29][O:28][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C:16](=[O:17])[CH2:15][CH2:9][C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8])[CH:27]=[CH:26]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18439041Ethyl 2-benzoyl-4-(6-methoxy-2-naphthyl)-4-oxobutanoate

Product 1

HCID 184390201-(6-Methoxy-2-naphthyl)-4-phenylbutane-1,4-dioneYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 2-benzoyl-4-(6-methoxy-2-naphthyl)-4-oxobutanoate (5.00 g, 12.8 mmol), prepared in the previous step, was dissolved in 300 mL of tetrahydrofuran. After complete dissolution of the ester, 1N NaOH solution (28.2 mL, 28.2 mmol) was added to the THF solution. The mixture was heated to gentle reflux for 24 hours, then allowed to cool back to ambient temperature. The mixture was acidified with 1N hydrochloric acid (105 mL) and allowed to stir for 15 minutes. The THF was then removed under reduced pressure and the residue was partitioned between methylene chloride and 1N HCl. The layers were separated, and the aqueous layer was extracted two times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure. Purification on silica gel (300 g, 200–300 mesh) using methylene chloride as the eluent gave 1-(6-methoxy-2-naphthyl)-4-phenylbutane-1,4-dione as a white solid (1.64 g, 40%), mp 163.5–164.5° C. Elemental Analysis for C21H18O3 Calc'd: C, 79.23; H, 5.70; N, 0.00. Found: C, 79.25; H, 5.70; N, 0.00.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto gentle reflux for 24 hours
  3. customThe THF was then removed under reduced pressure
  4. customthe residue was partitioned between methylene chloride and 1N HCl
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted two times with methylene chloride
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customPurification on silica gel (300 g, 200–300 mesh)

Sources & evidence

ORD record
ord-48a47c0483b2418c870966154ea02c0e
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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