Sulfuric Acid → n-Pentyl 2-[3-(3-Trifluoromethylphenyl)-5-Isoxazolyl]Benzoate

HRID 1706776Notes

Reaction equation

HRID 1706776 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.OS(O)(=O)=O>C(O)CCCC>[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][CH2:7][CH2:8][CH2:3][CH2:4][CH3:5])=[O:22])[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 13071263HCID 13071263, compound

Product 1

HCID 13125670n-Pentyl 2-[3-(3-Trifluoromethylphenyl)-5-Isoxazolyl]Benzoate

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A solution of 3'-(m-trifluoromethylphenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one (10 g., 0.03 mole) and concentrated H2SO4 (1 ml.) in n-pentyl alcohol (150 ml.) was held at reflux for 14 hours, cooled and poured into 300 ml. of ice water. The mixture was extracted with 600 ml. of ether. The ethereal solution was washed two times with water, dried over CaSO4 and concentrated under vacuum to give 12.05 g. of product as a yellow oil (99%). The oil was chromatographed on silica gel using ethyl acetate as the eluant. 8.4 g. of colorless oil was collected; ir (CHCl3) 1725 cm-1 ; nD25 =1.537.

Workup

  1. temperatureat reflux for 14 hours
  2. temperaturecooled
  3. additionpoured into 300 ml
  4. extractionThe mixture was extracted with 600 ml
  5. washThe ethereal solution was washed two times with water
  6. dry with materialdried over CaSO4
  7. concentrationconcentrated under vacuum
  8. customto give 12.05 g
  9. customThe oil was chromatographed on silica gel
  10. customof colorless oil was collected

Sources & evidence

ORD record
ord-37f9e52da6634faa9c47918e988320bc
Source dataset
uspto-grants-1980_06
Patent number
US04208510

Reaction notes

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