Hydrochloric Acid → 1,1-Diphenylacetone
Reaction equation
FC(F)(F)C1C=[C:5]([CH2:13][O:14]CC#N)C=C(C(F)(F)F)C=1.[Li][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([Li])CCC.C1(CC2C=CC=CC=2)C=CC=CC=1.Cl>CCCCCC.C(OCC)C.C(OCC)(=O)C>[C:22]1([CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:13](=[O:14])[CH3:5])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
To a cooled (-80° C.) solution of ((3,5-bis(trifluoromethyl)phenyl)methyloxy)acetonitrile (0.51 g; Example 1a, Method B(i) was added 0.42M lithio diphenylmethane (10 ml; prepared by addition of 2.5M n-butyl lithium in hexane (10 ml) to a cooled (-80° C.) solution of diphenylmethane (4.2 g) in diethyl ether (5 ml), followed by warming to room temperature for 3 hours). The solution was warmed to room temperature for 0.5h and then 1M-hydrochloric acid (10 ml) and ethyl acetate were added and the organic phase washed with saturated brine and dried (MgSO4). After evaporation in vacuo the residue was chromatographed on silica gel (eluting with 5% ethyl acetate in hexane ) to give 1-(3,5-bis(triflouromethyl)phenyl)methyloxy)-3,3-diphenyl acetone as an oil which gave an identical 1H NMR spectrum to the material prepared by Method A.
Workup
- washthe organic phase washed with saturated brine
- dry with materialdried (MgSO4)
- customAfter evaporation in vacuo the residue
- customwas chromatographed on silica gel (eluting with 5% ethyl acetate in hexane )
Sources & evidence
- ORD record
- ord-5043b7a381d4458fbaf08ecf3dc97c9c
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05563161
Reaction notes
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