Potassium Dichromate → 3'-METHOXY-3-PHENYLPROPIOPHENONE

HRID 481162Notes

Reaction equation

HRID 481162 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]([OH:29])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=[CH:18][CH:19]=1>O.S(=O)(=O)(O)O.CCOCC>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:20](=[O:29])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 24502Potassium DichromateHCID 15524231HCID 15524231, compound

Product 1

HCID 112071953'-METHOXY-3-PHENYLPROPIOPHENONEYield 83.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

14.9 g (0.05 mole) of potassium dichromate in a mixture of 50 ml of water and 10 ml of concentrated sulfuric acid were added to a solution of 34 g (0.14 mole) of 1-(3-methoxyphenyl)-3-phenylpropan-1-ol in 500 ml of ether while cooling with ice and stirred overnight at 20° C. The aqueous, green phase was separated and extracted twice with 100 ml of ether each time. The combined ether extracts were dried over sodium sulfate and the solvent was then removed in vacuo. 28.0 g (83%) of the compound 1-(methoxyphenyl)-3-phenylpropan-1-one were obtained as a yellow oil, which was reacted further without prior purification.

Workup

  1. temperaturewhile cooling with ice
  2. customThe aqueous, green phase was separated
  3. extractionextracted twice with 100 ml of ether each time
  4. dry with materialThe combined ether extracts were dried over sodium sulfate
  5. customthe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-592d635826f04e7fb005ac5fb930fe88
Source dataset
uspto-grants-2003_11
Patent number
US06653508B2

Reaction notes

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