Acetic Anhydride → 1-(2,6-dihydroxyphenyl)-2-methyl-1-propanone O-acetyloxime

HRID 527534Notes

Reaction equation

HRID 527534 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[N:13][OH:14])[CH:10]([CH3:12])[CH3:11].[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[C:15]([O:14][N:13]=[C:9]([C:3]1[C:4]([OH:8])=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1])[CH:10]([CH3:12])[CH3:11])(=[O:17])[CH3:16]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 1363786541-(2,6-Dihydroxyphenyl)-2-methyl-1-propanone oxime2×

Product 1

HCID 1363786551-(2,6-dihydroxyphenyl)-2-methyl-1-propanone O-acetyloximeYield 32.7%

Procedure

1-(2,6-dihydroxyphenyl)-2-methyl-1-propanone oxime (Intermediate 38, 320 mg) was stirred in acetic anhydride (0.928 ml, 9.84 mmol) at room temperature for 1 hour. After removal of the volatiles, the crude was washed with water, filtered and dried. The residue obtained was charged on a silica gel column (Biotage SP1 system) and eluted with Cyhexane/ethyl acetate (from 100/0 to 0/100) to afford the title compound (127 mg).

Workup

  1. customAfter removal of the volatiles
  2. washthe crude was washed with water
  3. filtrationfiltered
  4. customdried
  5. customThe residue obtained
  6. additionwas charged on a silica gel column (Biotage SP1 system)
  7. washeluted with Cyhexane/ethyl acetate (from 100/0 to 0/100)

Sources & evidence

ORD record
ord-951341dc2bf7489ab8d50e65c3dc7e09
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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