Hydrochloric Acid → HCID 54372346, compound

HRID 1415219Notes

Reaction equation

HRID 1415219 reaction equation
[C:1]([CH:4]1[C:8](=[O:9])[CH2:7][CH2:6][C:5]1=[O:10])(=[O:3])[CH3:2].[CH:11]1[C:16]([CH:17]=O)=[CH:15][C:14]2[O:19][CH2:20][O:21][C:13]=2[CH:12]=1.N1CCOCC1.Cl>O.CS(C)=O>[CH2:20]1[O:21][C:13]2[CH:12]=[CH:11][C:16]([CH:17]=[CH:2][C:1]([CH:4]3[C:8](=[O:9])[CH2:7][CH2:6][C:5]3=[O:10])=[O:3])=[CH:15][C:14]=2[O:19]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 8438PiperonalHCID 3364732-Acetyl-1,3-cyclopentanedione

Product 1

HCID 54372346HCID 54372346, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-Acetyl-1,3-cyclopentanedione (3.39 g.) was treated with piperonal (4.79 g.) in 60 ml. of dimethylsulfoxide in the presence of 5 ml. of morpholine at 85° C for 45 minutes. After cooling, the reaction mixture was poured into 150 ml. of water containing 7 ml. of conc. hydrochloric acid. Deposited crystals were separated by filtration and washed with water, and dried. 2-(3,4-Methylenedioxycinnamoyl)-1,3-cyclopentanedione (3.23 g.) was obtained in a yellow crystalline form, which showed mp. 181° - 182° C. after recrystallization from a mixed solvent of dioxane and ethanol.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into 150 ml
  3. customDeposited crystals were separated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6ab0240161514a6d84555c88b5612f79
Source dataset
uspto-grants-1977_01
Patent number
US04003936

Reaction notes

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