Sodium Carbonate → 1-Methylthio-3,3-dimethyl-2-butanone oxime

HRID 1111581Notes

Reaction equation

HRID 1111581 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][S:5][CH3:6].Cl.[NH2:11][OH:12].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=[N:11][OH:12])[CH2:4][S:5][CH3:6]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1701682-Butanone, 3,3-dimethyl-1-(methylthio)-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 382321-Methylthio-3,3-dimethyl-2-butanone oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 20.4 g (0.14 mol) of 3,3-dimethyl-1-methylthio-2-butanone, 19.6 g (0.28 mol) of hydroxylamine hydrochloride and 14.8 g (0.14 mol) of anhydrous sodium carbonate in 140 ml of 95% ethanol and 80 ml of water was heated at reflux for 16 hr. The resulting nearly colorless solution was stripped of volatiles on a rotary evaporator to yield a two layered liquid residue. This residue was extracted with four portions of ethyl acetate. The organic extract was dried over magnesium sulfate, filtered from the drying agent and stripped of solvent. Distillation of the residue gave the desired product as a colorless liquid, b. 83° C./0.6 mm Hg, nD22 1.4989.

Workup

  1. temperatureat reflux for 16 hr
  2. customThe resulting nearly colorless solution was stripped of volatiles on a rotary evaporator
  3. customto yield a two layered liquid residue
  4. extractionThis residue was extracted with four portions of ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered from the drying agent
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-5b8b9bb6627447e9aacace9f473f3af6
Source dataset
uspto-grants-1978_10
Patent number
US04118389

Reaction notes

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