Acetic Acid → 6-Methoxy-3-methylbenzo[d]isoxazole-7-carbaldehyde

HRID 594260Notes

Reaction equation

HRID 594260 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[O:4][N:3]=1.[CH2:12]1N2CN3CN(C2)CN1C3.Cl.[C:23](O)(=[O:25])C>>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[C:10]=1[CH:23]=[O:25]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 1354978903-Methyl-1,2-benzisoxazol-6-ol

Product 1

HCID 824037016-Methoxy-3-methylbenzo[d]isoxazole-7-carbaldehyde

Procedure

To a solution of commercially available 3-methylbenzo[d]isoxazol-6-ol (1.125 g; 7.54 mmol) in acetic acid (22.5 ml) was added hexamethylenetetramine (4.500 g; 32.09 mmol), and the resulting mixture was heated over a steam-bath for 6 h. The resulting hot mixture was then treated with 6 M aq. HCl (20 ml), and the heating was continued for 30 min. The solid obtained on dilution of the reaction mixture was filtered, and recrystallised from aq. MeOH to give the desired 6-hydroxy-3-methylbenzo[d]isoxazole-7-carbaldehyde as a yellow solid. LC-MS (conditions D): tR=0.79 min.; [M+H]+: 177.98 g/mol.

Workup

  1. temperaturethe resulting mixture was heated over a steam-bath for 6 h
  2. customThe solid obtained on dilution of the reaction mixture
  3. filtrationwas filtered
  4. customrecrystallised from aq. MeOH

Sources & evidence

ORD record
ord-93cb3a49d9f74287ad5b715d5936c208
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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