Hydrochloric Acid → 5,5-Diphenyl-2-cyclopentenyl acetate

HRID 1657269Notes

Reaction equation

HRID 1657269 reaction equation
[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:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:19]([O:12][CH:11]1[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH:9]=[CH:10]1)(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 100371165,5-Diphenyl-2-cyclopenten-1-ol

Product 1

HCID 100163975,5-Diphenyl-2-cyclopentenyl acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 5,5-diphenyl-2-cyclopenten-1-ol (0.70 g) in pyridine (5 ml) were added acetic anhydride (0.84 ml) and catalytic amount of 4-dimethylaminopyridine at room temperature. After being stirred for 30 minutes, the pH of the reaction mixture was adjusted to 1.0 with diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give 5,5-diphenyl-2-cyclopentenyl acetate (0.82 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

Sources & evidence

ORD record
ord-dc36c2bf594c4c53906a31b860f14c04
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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