Citric Acid → 1,3-Bis(4-methoxyphenyl)-1,3-propanedione

HRID 2087015Notes

Reaction equation

HRID 2087015 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[C:12](Cl)(=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH2:10][C:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:21])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 74764'-MethoxyacetophenoneHCID 7477p-Anisoyl chloride

Product 1

HCID 875961,3-Bis(4-methoxyphenyl)-1,3-propanedione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4′-methoxyacetophenone (1.0 equiv.) in THF at −78° C. was added dropwise 1.5 equiv. of [(CH3)2Si]2NLi. The solution was stirred for 1 h at −78° C., followed by addition of 1.2 equiv. of p-anisoyl chloride. The reaction mixture was stirred for 10 min at −78° C. and then for 22 h at rt, acidified with 10% citric acid, and extracted with EtOAc. The combined organic layers were washed with water and dried over Na2SO4. Removal of solvent in vacuo provided a crude solid which was purified by flash chromatography (CH2Cl2) to give 1,3-di(4-methoxyphenyl)propane-1,3-dione.

Workup

  1. stirringThe reaction mixture was stirred for 10 min at −78° C.
  2. waitfor 22 h at rt
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. customRemoval of solvent in vacuo
  7. customprovided a crude solid which
  8. customwas purified by flash chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-63204477f9974ee9a46cd713f80529cc
Source dataset
uspto-grants-2004_04
Patent number
US06727273B2

Reaction notes

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