Acetic Anhydride → HCID 19756108, compound

HRID 1587696Notes

Reaction equation

HRID 1587696 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:14][C:15]1[CH:16]=[CH:17][CH:18]=C(C)[N+:20]=1[O-])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>C(O)(=O)C>[C:5]([O:4][CH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([O:14][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[N:20]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67852818HCID 67852818, compound

Product 1

HCID 19756108HCID 19756108, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

An amount 40 ml of acetic anhydride was stirred at about 115° C. and a solution of 5.50 g of 6-hexyloxy-α-picoline N-oxide in 20 ml of glacial acetic acid was dropwise added over about one hour. After the dropwise addition, the mixture was stirred at 130° C. for 5 hours, acetic acid and acetic anhydride were removed by concentration under a reduced pressure, the reaction mixture was dissolved in ether, and the remaining acetic acid was neutralized with a sodium hydrogen carbonate solution. After extraction with ether and concentration under a reduced pressure, the residue was separated by silica gel column chromatography (ethyl acetate:hexane=1:9) to give 6.85 g of the desired product (yield 100%).

Workup

  1. additionAfter the dropwise addition
  2. customacetic acid and acetic anhydride were removed by concentration under a reduced pressure
  3. dissolutionthe reaction mixture was dissolved in ether
  4. extractionAfter extraction
  5. concentrationwith ether and concentration under a reduced pressure
  6. customthe residue was separated by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-5dc1b7c46b8b480eb6564f0bff5939bd
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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