Hydrochloric Acid → 3,6-Dimethyl-1,2-benzisoxazol-4-ol

HRID 527519Notes

Reaction equation

HRID 527519 reaction equation
C(O[N:5]=[C:6]([C:8]1[C:13]([OH:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=1[OH:16])[CH3:7])(=O)C.Cl>N1C=CC=CC=1>[CH3:7][C:6]1[C:8]2=[C:13]([OH:14])[CH:12]=[C:11]([CH3:15])[CH:10]=[C:9]2[O:16][N:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1363786491-(2,6-dihydroxy-4-methylphenyl)ethanone O-acetyloxime2×

Product 1

HCID 1363786503,6-Dimethyl-1,2-benzisoxazol-4-olYield 47.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1-(2,6-dihydroxy-4-methylphenyl)ethanone O-acetyloxime (Intermediate 18, 1.0 g) pyridine (10 ml) was added and the reaction mixture was stirred at reflux under N2 for 2 hours. After the addition of HCl (10.0 ml of a 5M aqueous solution), the mixture was extracted 3 times with Et2O and the gathered organic phases were washed with HCl (1M). The separated organic phase was then dried over sodium sulphate, filtered and evaporated to afford 345 mg of the title compound.

Workup

  1. temperatureat reflux under N2 for 2 hours
  2. extractionwas extracted 3 times with Et2O
  3. washthe gathered organic phases were washed with HCl (1M)
  4. dry with materialThe separated organic phase was then dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-02c400451800446282b611be79cab951
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…