Acetic Anhydride → [(E)-1-(2-hydroxy-3-methylphenyl)ethylideneamino] acetate

HRID 873881Notes

Reaction equation

HRID 873881 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1/[C:9](=[N:11]/[OH:12])/[CH3:10].[CH3:13][C:14](OC(C)=O)=[O:15]>>[C:14]([O:12]/[N:11]=[C:9](/[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[OH:1])\[CH3:10])(=[O:15])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 1370147826-[1-(Hydroxyamino)ethylidene]-2-methylcyclohexa-2,4-dien-1-one

Product 1

HCID 137014778[(E)-1-(2-hydroxy-3-methylphenyl)ethylideneamino] acetateYield 96%

Procedure

(E)-1-(2-hydroxy-3-methylphenyl)ethanone oxime (Step 46.2) (5.5 g, 30 mmol) was added into Ac2O (48.1 mL, 509 mmol) under argon and the resulting mixture was stirred at RT for 1.5 hr. The reaction was concentrated to 10 mL volume under reduced pressure; the resulting suspension was diluted with cold water and stirred at RT until a fine precipitate occurred. The resulting solid was filtrated off, washed with water and dried to afford the title product (6.03 g, 28.8 mmol, 96% yield) as colorless solid. tR: 1.08 min (LC-MS 2); ESI-MS: 208 [M+H]+; Rf=0.60 (hexane/EtOAc 1:1).

Workup

  1. concentrationThe reaction was concentrated to 10 mL volume under reduced pressure
  2. additionthe resulting suspension was diluted with cold water
  3. stirringstirred at RT until a fine precipitate
  4. filtrationThe resulting solid was filtrated off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e89e4cc7593b4486a4726ba077112c6a
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…