Methanol → Methyl 2-[3-(p-Chlorophenyl)-5-Isoxazolyl]Benzoate

HRID 1706774Notes

Reaction equation

HRID 1706774 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]3([C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14](=[O:21])[O:13]3)[O:10][N:9]=2)=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:27]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]([O:13][CH3:27])=[O:21])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 13071253HCID 13071253, compound

Product 1

HCID 13125672Methyl 2-[3-(p-Chlorophenyl)-5-Isoxazolyl]Benzoate

Procedure

A solution of 6.3 g. (0.020 mole) of 3'-(p-chlorophenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one, 2 ml. of concentrated H2SO4 and 300 ml. of methanol was stirred at reflux for 20 hours. The cooled solution was poured into ice water (3 liters) and extracted with ether. The combined organic extracts were washed twice with water, dried over CaSO4 and concentrated under vacuum to yield 5.8 g. of colorless crystals (88%) of product. Recrystallization from hexane afforded 5.4 g. of an analytically pure sample; m.p. 89.5°-91° C.

Workup

  1. temperatureat reflux for 20 hours
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed twice with water
  4. dry with materialdried over CaSO4
  5. concentrationconcentrated under vacuum
  6. customto yield 5.8 g
  7. customRecrystallization from hexane
  8. customafforded 5.4 g

Sources & evidence

ORD record
ord-7738a9c5fa8e4f4d832ef8c01b8cab4a
Source dataset
uspto-grants-1980_06
Patent number
US04208510

Reaction notes

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