Hydrochloric Acid → HCID 54124309, compound

HRID 1415220Notes

Reaction equation

HRID 1415220 reaction equation
[C:1]([CH:4]1[C:8](=[O:9])[CH2:7][CH2:6][C:5]1=[O:10])(=[O:3])[CH3:2].[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:15]=O.N1CCOCC1.Cl>O.C(O)C>[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:15]=[CH:2][C:1]([CH:4]1[C:8](=[O:9])[CH2:7][CH2:6][C:5]1=[O:10])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 12127IsovanillinHCID 3364732-Acetyl-1,3-cyclopentanedione

Product 1

HCID 54124309HCID 54124309, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Acetyl-1,3-cyclopentanedione (3.83 g.) was treated with 5.0 g. of 3-hydroxy-4-methoxybenzaldehyde in 120 ml. of ethanol in the presence of 5 ml. of morpholine under reflux for 5 hours. After cooling, the reaction mixture was poured into 200 ml. of water containing 8 ml. of conc. hydrochloric acid. Deposited crystals were separated by filtration, washed with water and ethanol successively, and dried. 2-(3-Hydroxy-4-methoxycinnamoyl)-1,3-cyclopentanedione (5.46 g.) was obtained, in the form of yellow crystals which showed mp. 137°-139° C. after recrystallisation from a mixed solvent of ethanol and dioxane.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into 200 ml
  3. customDeposited crystals were separated by filtration
  4. washwashed with water and ethanol successively
  5. customdried

Sources & evidence

ORD record
ord-c103825e3ccf495bbd7a3369715b113d
Source dataset
uspto-grants-1977_01
Patent number
US04003936

Reaction notes

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