Acetic Acid → HCID 10976374, compound

HRID 1108051Notes

Reaction equation

HRID 1108051 reaction equation
N1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:6](=[CH:13]C(=O)C)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:17]1[CH2:21]C=C[CH:18]=1.C(O)(=O)C>CO.C(OCC)C.O>[CH3:2][C:3]1[CH2:13][CH:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:5]2[C:4]=1[CH:18]=[CH:17][CH:21]=2

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7612CyclopentadieneHCID 159094-Phenyl-3-Buten-2-oneHCID 31268Pyrrolidine

Product 1

HCID 10976374HCID 10976374, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

208 g (359 mmol) of pyrrolidine are added dropwise at 0° C. over a period of 45 minutes to a mixture of 35.0 g (239 mmol) of benzalacetone and 38.1 g (717 mmol) of cyclopentadiene in 300 ml of methanol. The red reaction solution is stirred for 40 minutes at room temperature and is subsequently admixed at 0° C. with 19 g (346 mmol) of glacial acetic acid. After addition of 300 ml of water and 500 ml of diethyl ether, the product is extracted. The aqueous phase is extracted twice with 250 ml each time of diethyl ether, the combined ether phases are dried over MgSO4 and the solvent is removed under reduced pressure. The crude product is distilled in an oil pump vacuum, giving 24.1 g (52%) of 4-methyl-6-phenyl-5,6-dihydropentalene.

Workup

  1. extractionthe product is extracted
  2. extractionThe aqueous phase is extracted twice with 250 ml each time of diethyl ether
  3. dry with materialthe combined ether phases are dried over MgSO4
  4. customthe solvent is removed under reduced pressure
  5. distillationThe crude product is distilled in an oil pump vacuum

Sources & evidence

ORD record
ord-f8428cea1a464a1785c8fbce5f5120a4
Source dataset
uspto-grants-2000_05
Patent number
US06063949

Reaction notes

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