Hydrochloric Acid → 5,5-Diphenyl-2-cyclopenten-1-ol

HRID 1657268Notes

Reaction equation

HRID 1657268 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11](=[O:12])[CH:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)(=O)C.Cl>C1(C)C=CC=CC=1>[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]([OH:12])[CH:10]=[CH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 104665565,5-Diphenyl-2-cyclopenten-1-oneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 100371165,5-Diphenyl-2-cyclopenten-1-olYield 48.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 5,5-diphenyl-2-cyclopenten-1-one (5.0 g) in toluene (25 ml) was added dropwise diisobutylaluminum hydride (15 ml, 1.5M solution in toluene) for 10 minutes at -78° C. to -50° C. After 30 minutes, ethyl acetate (5 ml) was added to the resultant yellow solution. The solution was acidified to pH 1 with 6N hydrochloric acid (20 ml) and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with methylene chloride as an eluent and further purified by bulb to bulb distillation to give 5,5-diphenyl-2-cyclopenten-1-ol (2.46 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with methylene chloride as an eluent
  6. distillationfurther purified by bulb to bulb distillation

Sources & evidence

ORD record
ord-434a4467bdff42e4b99e7e063fb4814c
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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