Hexane → 1,2-Diphenylpropan-1-one

HRID 1249021Notes

Reaction equation

HRID 1249021 reaction equation
CS([O:5][C@@H:6](C)[C:7]([C:15]1C=CC=CC=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)O)(=O)=O.[CH3:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C([Al](CC)CC)C>C(Cl)Cl.P([O-])([O-])([O-])=O.C(OCC)(=O)C>[C:24]1([C:6](=[O:5])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:15])[CH:23]=[CH:22][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 8058HexaneHCID 13198946HCID 13198946, compoundHCID 16682930Triethylaluminum

Product 1

HCID 2385181,2-Diphenylpropan-1-oneYield 96%

Reagents, catalysts & solvents 3

HCID 1061PhosphateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (S)-2-methanesulfonyloxy-1,1-diphenyl-1-propanol (153 mg, 0.5 mmol) present in 5 ml of CH2Cl2 in Referential example 3 was added a hexane solution of triethylaluminum (0.6 mmol, 0.7 ml) slowly at -78° C. The color of the solution changed to yellow. After stirred further for 30 minutes, the reaction was stopped with three drops of phosphate buffer solution having a pH value of 7. The suspension obtained was diluted with ethyl acetate, dried over anhydrous Na2SO4, filtered and concentrated. Oily residue was subjected to the chromatography treatment with Florisil column to obtain 1,2-diphenyl-1-propanone (100 mg, 96%).

Workup

  1. customThe suspension obtained
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-40e76a439989495cac5efb25c3da2ee9
Source dataset
uspto-grants-1986_12
Patent number
US04628120

Reaction notes

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