m-Chloroperbenzoic acid → 6-butoxy-alpha-picoline N-oxide

HRID 1587691Notes

Reaction equation

HRID 1587691 reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[C:10]([CH3:12])[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:21])C=1>C(OCC)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:12])[N+:11]=1[O-:21])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 197561256-Butoxy-alpha-picoline

Product 1

HCID 678527606-butoxy-alpha-picoline N-oxideYield 51.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 19.0 g (0.12 mol) of 6-butoxy-α-picoline dissolved in 250 ml of diethyl ether was portionwise added 23.8 g (0.14 mol) of m-chloroperbenzoic acid under ice-cooling. After standing under ice-cooling for one hour, the mixture was further left to stand at room temperature for several days. The reaction mixture was extracted with water and then adjusted to pH=11 with an addition of sodium carbonate. After extraction with chloroform, the extract was concentrated under a reduced pressure to give 11.2 g of the desired product.

Workup

  1. temperaturecooling
  2. temperaturecooling for one hour
  3. waitthe mixture was further left
  4. waitto stand at room temperature for several days
  5. extractionThe reaction mixture was extracted with water
  6. additionadjusted to pH=11 with an addition of sodium carbonate
  7. extractionAfter extraction with chloroform
  8. concentrationthe extract was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-ecf1ec186948484f845f8d0849ebd3b1
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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