Sulfuric Acid → 2-[3-(2-Methylphenyl)-5-Isoxazolyl]-Benzoic Acid

HRID 1706778Notes

Reaction equation

HRID 1706778 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:12][C:11]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[O:13]2)[O:10][N:9]=1.O1CCOCC1.S(=O)(=O)(O)O>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:12]=[C:11]([C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]([OH:21])=[O:13])[O:10][N:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 13071254HCID 13071254, compound

Product 1

HCID 131256652-[3-(2-Methylphenyl)-5-Isoxazolyl]-Benzoic AcidYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 0.26 g. of 3'-(2-methylphenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one, 4ml. of water, 4 ml. of dioxane and 0.10 ml. of concentrated sulfuric acid was stirred at reflux for one hour, allowed to cool and diluted with 15 ml. of water. The resultant oil was stirred several minutes to give 0.24 g. of white solid; m.p. 162°-163.5° C. in 92% yield.

Workup

  1. additionA mixture of 0.26 g
  2. temperatureat reflux for one hour
  3. temperatureto cool
  4. additiondiluted with 15 ml
  5. customto give 0.24 g

Sources & evidence

ORD record
ord-49bccf5b6ccc4bc88b2673a52cdab2b2
Source dataset
uspto-grants-1980_06
Patent number
US04208510

Reaction notes

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