Acetic Acid → HCID 14470389, compound

HRID 1108052Notes

Reaction equation

HRID 1108052 reaction equation
N1CCCC1.[CH:6](=[CH:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:22]1[CH2:26][CH:25]=[CH:24][CH:23]=1.C(O)(=O)C>CO.C(OCC)C.O>[C:7]1([C:6]2[CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:24]3[C:25]=2[CH:26]=[CH:22][CH:23]=3)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7189CinnamoylbenzeneHCID 7612CyclopentadieneHCID 31268Pyrrolidine

Product 1

HCID 14470389HCID 14470389, compoundYield 55.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

230 g (324 mmol) of pyrrolidine are added dropwise at 0° C. over a period of 45 minutes to a mixture of 45.0 g (216 mmol) of benzalacetophenone and 42.8 g (648 mmol) of cyclopentadiene in 350 ml of methanol. The red reaction solution is stirred for 40 minutes at room temperature and is subsequently admixed at 0° C. with 21 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 30.5 g (55%) of 4,6-diphenyl-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-9243767b803d4405ae5d665f63cafd2b
Source dataset
uspto-grants-2000_05
Patent number
US06063949

Reaction notes

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