2-acetylcyclopentane-1,3-dione

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. After cooling the reaction mixture was poured into 300 ml Deposited crystals were separated by filtration washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. After cooling the reaction mixture was poured into 200 ml Deposited crystals were separated by filtration washed with water and ethanol successively dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. After cooling the reaction mixture was poured into 150 ml Deposited crystals were separated by filtration washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Acetyl-1,3-cyclopentanedione (3.13 g.) was treated with 3,4-dichlorobenzaldehyde (4.36 g.) in 140 ml. of ethanol under reflux for 4 hours in the presence of 5 ml. of morpholine. 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-Dichlorocinnamoyl)-1,3-cyclopentanedione (2.48 g., 37%) was obtained which showed mp. 190°- 191° C. after recrystallization from dioxane. After cooling the reaction mixture was poured into 150 ml Deposited crystals were separated by filtration washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. After cooling The solid was collected by filtration washed with water and ethanol successively it was then dried