Hydrochloric Acid → HCID 54523957, compound

HRID 1415217Notes

Reaction equation

HRID 1415217 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:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=1[O:20][CH3:21].N1CCOCC1.Cl>CS(C)=O>[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[CH:2][C:1]([CH:4]2[C:8](=[O:9])[CH2:7][CH2:6][C:5]2=[O:10])=[O:3])=[CH:14][C:13]=1[O:20][CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1183VanillinHCID 8083MorpholineHCID 3364732-Acetyl-1,3-cyclopentanedione

Product 1

HCID 54523957HCID 54523957, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Acetyl-1,3-cyclopentanedione (3.03 g.) was treated with 4-hydroxy-3-methoxybenzaldehyde (5.05 g.) in 50 ml. of dimethylsulfoxide at 80° C for 13 minutes in the presence of 4 ml. of morpholine. After cooling, 80 ml. of 1 N hydrochloric acid was added to the reaction mixture, depositing a crystalline product. The solid was collected by filtration, and washed with water and ethanol successively, and it was then dried. The Claiseu-Schmidt condensation product, 2-(4-hydroxy-3-methoxycinnamoyl)-1,3-cyclopentanedione, (1.3 g.) was obtained in an orange crystalline form, which showed mp. 274°- 275° C after recrystallization from dioxane.

Workup

  1. temperatureAfter cooling
  2. filtrationThe solid was collected by filtration
  3. washwashed with water and ethanol successively
  4. customit was then dried

Sources & evidence

ORD record
ord-bb11280a56ac4ea09b75dd2526e6d08f
Source dataset
uspto-grants-1977_01
Patent number
US04003936

Reaction notes

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