Citric Acid → 1,3-Bis(4-methoxyphenyl)-2-phenylpropane-1,3-dione

HRID 2087014Notes

Reaction equation

HRID 2087014 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[C:18](Cl)(=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:17])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:27])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 7477p-Anisoyl chlorideHCID 2310931-(4-Methoxyphenyl)-2-phenylethan-1-one

Product 1

HCID 127946981,3-Bis(4-methoxyphenyl)-2-phenylpropane-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-(4-methoxyphenyl)-2-phenylethan-1-one (1.0 equiv.) in THF at −78° C. was added dropwise 1.5 equiv. of [(CH3)2Si]NLi. 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-bis(4-methoxyphenyl)-2-phenylpropane-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-862054b8094d4357bc1c6caf7364996e
Source dataset
uspto-grants-2004_04
Patent number
US06727273B2

Reaction notes

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