Water → HCID 19774600, compound

HRID 1613917Notes

Reaction equation

HRID 1613917 reaction equation
[Na].[C:2]1([C:8](=O)[CH2:9][CH2:10][C:11](=O)[CH3:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]1[CH2:19][CH:18]=[CH:17][CH:16]=1.O>CO>[CH3:12][C:11]1[CH:10]=[CH:9][C:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:15]2[C:16]=1[CH:17]=[CH:18][CH2:19]2

Participants

6

Reactant 4

HCID 962WaterHCID 7612CyclopentadieneHCID 1363711-Phenyl-1,4-pentanedioneHCID 5360545Sodium

Product 1

HCID 19774600HCID 19774600, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

5 g (0.21 mol}of sodium were dissolved in 100 ml of methanol in a Schlenk tube and the solution was cooled to 0° C. A mixture of 15.8 g (0.84 mol) of 1-phenyl-1,4-pentanedione and 7.3 ml (5.8 g, 0.08 mol) of cyclopentadiene was added dropwise in the course of 15 minutes. The red solution was stirred at room temperature overnight, hydrolyzed with 200 ml of water and extracted five times with 75 ml of petroleum ether each time. The combined organic extracts were filtered and concentrated to dryness and the residue was subjected to fractional distillation.

Workup

  1. additionwas added dropwise in the course of 15 minutes
  2. extractionextracted five times with 75 ml of petroleum ether each time
  3. filtrationThe combined organic extracts were filtered
  4. concentrationconcentrated to dryness
  5. distillationthe residue was subjected to fractional distillation

Sources & evidence

ORD record
ord-c5116fce7cf141abaf85028dc9f11d82
Source dataset
uspto-grants-1993_03
Patent number
US05194619

Reaction notes

Loading…