HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sulfuric Acid → 3-(4-Methylphenyl)-5-butyrylisoxazole

HRID 1440331
Notes
Print preview

Reaction equation

HRID 1440331 reaction equation
[H-].[Na+].C(C(C(OC1C=CC=CO1)=O)C(OC1C=CC=CO1)=O)C.[CH2:24]([CH:26]([C:30]([OH:32])=O)C(O)=O)[CH3:25].O1C=CCCC1.S(=O)(=O)(O)O.C(C(C([O-])=O)C([O-])=O)C.C(OC1C=CC=CO1)(=O)CC(OC1C=CC=CO1)=O.[Na].[CH3:73][C:74]1[CH:79]=[CH:78][C:77]([C:80]2[CH:84]=[C:83](C(Cl)=O)[O:82][N:81]=2)=[CH:76][CH:75]=1>C1C=CC=CC=1.O.C(O)(=O)C.O1CCCC1>[CH3:73][C:74]1[CH:75]=[CH:76][C:77]([C:80]2[CH:84]=[C:83]([C:30](=[O:32])[CH2:26][CH2:24][CH3:25])[O:82][N:81]=2)=[CH:78][CH:79]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

13

Reactant 8

HCID 1118Sulfuric AcidHCID 80803,4-dihydro-2H-pyranHCID 11756Ethylmalonic acidHCID 24758Sodium hydrideHCID 6950106EthylpropanedioateHCID 19976934Dipyranyl ethylmalonateHCID 53715915
3-(4-Methylphenyl)isoxazole-5-carboxylic acid chloride
HCID 67715643Sodium dipyranyl malonate

Product 1

HCID 199769533-(4-Methylphenyl)-5-butyrylisoxazole

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of benzene, 2.6 g (57.5 mmol) of 60% sodium hydride were added to dipyranyl ethylmalonate which had been prepared from 5.7 g (43.2 mmol) of ethylmalonic acid, 9.0 g (107.1 mmol) of 3,4-dihydropyran and 1 droplet of concentrated sulfuric acid. At 40°-50° C., the ethylmalonate was converted to sodium dipyranyl malonate, to which a tetrahydrofuran solution of 3-(4-methylphenyl)isoxazole-5-carboxylic acid chloride synthesized above in the procedure (3) was added dropwise at room temperature. They were reacted for 3 hours. The reaction mixture was added with 10 ml of acetic acid and then heated under reflux for 6 hours. The mixture thus obtained was added into water and then extracted with benzene. The benzene extract was washed successively with an aqueous solution of sodium hydrogencarbonate and water. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off. Hexane was added to the residue, and 3-(4-methylphenyl)-5-butyrylisoxazole precipitated as crystals was collected by filtration.

Workup

  1. customAt 40°-50° C.
  2. customsynthesized above in the procedure (3)
  3. additionwas added dropwise at room temperature
  4. customThey were reacted for 3 hours
  5. temperatureheated
  6. temperatureunder reflux for 6 hours
  7. customThe mixture thus obtained
  8. extractionextracted with benzene
  9. extractionThe benzene extract
  10. washwas washed successively with an aqueous solution of sodium hydrogencarbonate and water
  11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  12. distillationthe solvent was distilled off
  13. additionHexane was added to the residue, and 3-(4-methylphenyl)-5-butyrylisoxazole
  14. customprecipitated as crystals
  15. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-373eee14e52f4e4fbf79c7abb5aecdde
Source dataset
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05498619

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes