Methanol → Methyl 2-[3-(3-trifluoromethylphenyl)-5-isoxazolyl]benzoate

HRID 1706773Notes

Reaction equation

HRID 1706773 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:13][C:12]3([C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=[O:22])[O:14]3)[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.S(=O)(=O)(O)O.[CH3:30]O>>[F:23][C:2]([F:24])([F:1])[C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]([O:14][CH3:30])=[O:22])[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 13071263HCID 13071263, compound

Product 1

HCID 13018699Methyl 2-[3-(3-trifluoromethylphenyl)-5-isoxazolyl]benzoate

Procedure

A mixture of 2 g. (0.006 mole) of 3'-(m-trifluoromethylphenyl)-spiro[isobenzofuran-1(3H), 5'(4'H)-isoxazol]-3-one, 2 ml. of concentrated sulfuric acid and 50 ml. of methanol was heated at reflux for 17 hours. The solution was then poured into 100 g. of ice and extracted twice with 300 ml. of ether. The ether solutions were combined, washed twice with water saturated sodium chloride, and dried over CaSO4. Removal of the solvent gave 2 g. of colorless viscous liquid, which was crystallized from hexane at 0° C. to give colorless crystals; m.p. 46°-48° C.

Workup

  1. additionA mixture of 2 g
  2. temperatureat reflux for 17 hours
  3. additionThe solution was then poured into 100 g
  4. extractionof ice and extracted twice with 300 ml
  5. washwashed twice with water saturated sodium chloride
  6. dry with materialdried over CaSO4
  7. customRemoval of the solvent
  8. customgave 2 g
  9. customof colorless viscous liquid, which was crystallized from hexane at 0° C.
  10. customto give colorless crystals

Sources & evidence

ORD record
ord-749f7d7c5fc241ab9cb0caf4bf341adf
Source dataset
uspto-grants-1980_06
Patent number
US04208510

Reaction notes

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