Benzaldehyde → HCID 11506914, compound

HRID 1600368Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=O)=[CH:4][CH:3]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.S(=O)(=O)(O)O.[I-].[Na+].O.[NH2:27][NH2:28].[OH-].[Na+]>O>[C:12]1([C:11]2[CH:10]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)[NH:28][N:27]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 40 °C

Procedure

67.2 parts (0.5 mol) of 4-methylacetophenone and 53 parts (0.5 mol) of benzaldehyde were simultaneously added dropwise at 40° C. to 326.7 parts (2 mol) of 60% strength by weight sulfuric acid. The mixture was stirred at 40° C. for 2 hours and the phases were then separated. The sulfuric acid phase was initially introduced into the reaction flask with 0.5 part (0.0033 mol) of sodium iodide and the organic phase was simultaneously added dropwise at 100° C. in the course of 30 minutes with 25 parts (0.5 mol) of hydrazine hydrate. The mixture was stirred under reflux (114° C.) for 4 hours and then diluted with 250 parts of water. The mixture was neutralized with 477 parts (2.98 mol) of 25% strength by weight sodium hydroxide solution and filtered at room temperature. The filter residue was washed with water and dried. 111.2 parts of 3-phenyl-5-(4-methylphenyl)pyrazole having a purity of 94.7% (HPLC) were obtained, which corresponds to a yield of 90% of theory. M.p.:175° C.

Workup

customthe phases were then separated
stirringThe mixture was stirred
temperatureunder reflux (114° C.) for 4 hours
filtrationfiltered at room temperature
washThe filter residue was washed with water
customdried

Sources & evidence

ORD record: ord-7780e88f23474fd1b2ed7aa338293358
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05744614

Reaction notes

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