Acetone → Ethyl 4-nitrobenzylthioacetate

HRID 2285938

Reaktionsgleichung

Reaktionsgleichung von HRID 2285938
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C[C:13]([CH3:15])=[O:14].CCO[C:19]([CH2:21][SH:22])=O.C(=O)([O-])[O-].[K+].[K+]>CCOCC.O.[I-].[K+]>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][CH2:19][C:21]([O:14][CH2:13][CH3:15])=[S:22])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

8

Edukt 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 660114-Nitrobenzyl bromide

Produkt 1

HCID 54092468Ethyl 4-nitrobenzylthioacetateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 4875Potassium IodideKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

43.2 g (0.2 mol) of p-nitrobenzyl bromide, 200 ml of acetone, 0.2 g of potassium iodide, 24 ml of ethyl thioglycollate (that is to say a slight excess) and 27.6 g (0.2 mol) of potassium carbonate are introduced successively into a 1 liter three-necked flask. The mixture is heated under reflux for about 4 hours until the complete disappearance of the bromo derivative; the acetone is evaporated, the oil obtained is taken up in ether and in water, the ether phase is washed with a dilute NaOH solution, so as to eliminate the excess thiol, and then with a dilute HCl solution, and is dried over Na2SO4, and the solvent is evaporated. 49 g (yield: 95%) of the stated product are obtained, which is in the form of an orange-coloured oil.

Aufarbeitung

  1. additionare introduced successively into a 1 liter three-necked flask
  2. temperatureThe mixture is heated
  3. customthe acetone is evaporated
  4. customthe oil obtained
  5. washthe ether phase is washed with a dilute NaOH solution
  6. dry with materialwith a dilute HCl solution, and is dried over Na2SO4
  7. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-81193c2ac0604414b08ba8be037c0959
Quelldatensatz
uspto-grants-1982_04
Patentnummer
US04325964

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