Benzaldehyde → HCID 66718142, compound

HRID 1514668Notes

Reaction equation

HRID 1514668 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[O-]CC.[Na+].Cl>C(O)C>[C:12]1([C:7]2[C:6]([C:4]([OH:3])=[O:5])=[C:10](/[CH:11]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:9][N:8]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 70838Ethyl 5-methyl-3-phenylisoxazole-4-carboxylateHCID 2723922Sodium ethoxide

Product 1

HCID 66718142HCID 66718142, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid ethyl ester (2.28 g, 10 mmol) and benzaldehyde (1.01 mL, 10 mmol) in ethanol (15 mL) was added sodium ethoxide (0.74 g, 11 mmol) and the reaction mixture was heated under reflux for 10 min. Aqueous hydrochloric acid (1 M, 12 mL) was then added and after stirring for 15 min the precipitate was filtered and dried to afford the title compound as a light brown solid (2.0 g, 71%). MS: m/e=292.1 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 10 min
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-44a1910e2f1848b69673294c543eb47d
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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