Hydrochloric Acid → HCID 54027579, compound

HRID 1415221Notes

Reaction equation

HRID 1415221 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[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=O.N1CCOCC1.Cl>O.CS(C)=O>[OH:11][C:12]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[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 8991o-VanillinHCID 3364732-Acetyl-1,3-cyclopentanedione

Product 1

HCID 54027579HCID 54027579, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-Acetyl-1,3-cyclopentanedione (4.26 g.) was treated with 4.94 g. of 2-hydroxy-3-methoxybenzaldehyde in 100 ml. of dimethylsulfoxide in the presence of 6 ml. of morpholine at 85° C for 40 minutes. After cooling, the reaction mixture was poured into 300 ml. of water containing 12 ml. of conc. hydrochloric acid. Deposited crystals were separated by filtration and washed with water, and dried. 2-(2-Hydroxy-3-methoxycinnamoyl)-1,3-cyclopentanedione (4.40 g., 49%) was obtained in yellow crystalline state, which showed mp. 198° - 200° C. after recrystallization from a mixed solvent of dioxane and ethanol.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into 300 ml
  3. customDeposited crystals were separated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8cbf869a563a4bb1b4da9f57ce09c35f
Source dataset
uspto-grants-1977_01
Patent number
US04003936

Reaction notes

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