Isopropanol → HCID 86737440, compound

HRID 1389719Notes

Reaction equation

HRID 1389719 reaction equation
[CH:1](O)(C)C.[Na].[CH:6]1[CH2:10]C=[CH:8][CH:7]=1.[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)[CH3:12]>O.CO>[CH3:1][C:12]1[CH:8]=[CH:7][C:6](=[CH2:10])[C:11]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 7410AcetophenoneHCID 7612CyclopentadieneHCID 5360545Sodium

Product 1

HCID 86737440HCID 86737440, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a two-liter 3-necked flask are charged isopropyl alcohol (1000 ml), methanol (300 ml) and sodium (10 g). Freshly distilled cyclopentadiene (180 g) and acetophenone (261 g) are mixed and slowly added, with stirring, to the solution in the flask. The reaction is run at room temperature. After 11/2 hours, the addition is complete. The reaction mixture is mixed with water and the organic layer extracted into hexane. The hexane extract is washed with water and stripped. The crude methyl phenyl-fulvene is distilled (80°-85° C./0.1 mm) and the distillate is a ruby-red liquid.

Workup

  1. additionslowly added
  2. customis run at room temperature
  3. additionAfter 11/2 hours, the addition
  4. extractionthe organic layer extracted into hexane
  5. extractionThe hexane extract
  6. washis washed with water
  7. distillationThe crude methyl phenyl-fulvene is distilled (80°-85° C./0.1 mm)

Sources & evidence

ORD record
ord-d8c04603de994dce80341c065334ba6d
Source dataset
uspto-grants-1981_01
Patent number
US04246167

Reaction notes

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