Diethyl Ether → Ethyl 4-nitrobenzylthioacetate

HRID 2052407

Reaction equation

HRID 2052407 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(OCC)(=O)C[SH:14].C(=O)([O-])[O-].[K+].[K+].BrBr.[CH3:27][CH2:28][O:29][CH2:30][CH3:31]>O.[I-].[K+].CC(C)=O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][CH2:27][C:28]([O:29][CH2:30][CH3:31])=[S:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

9

Reactant 5

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 24408BromineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 54092468Ethyl 4-nitrobenzylthioacetateYield 95%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

43.2 g (0.2 mol) of p-nitrobenzylbromide, 200 ml of acetone, 0.2 g of potassium iodide, 24 ml of ethyl thioglycolate (namely a slight excess) and 27.6 g (0.2 mol) of potassium carbonate are successively introduced into a 1 liter 3-necked flask. The mixture is heated under reflux for about 4 hours until the bromine derivative completely disappears; the acetone is evaporated, the oil obtained is taken up in ether and in water, the ether phase is washed with a dilute solution of NaOH to remove the excess thiol, and then with a dilute solution of HCl, the solution is dried over Na2SO4 and the solvent is evaporated off. 49 g (yield: 95%) of the stated product, which is in the form of an orange coloured oil, are obtained.

Workup

  1. temperatureThe mixture is heated
  2. customthe acetone is evaporated
  3. customthe oil obtained
  4. washthe ether phase is washed with a dilute solution of NaOH
  5. customto remove the excess thiol
  6. dry with materialwith a dilute solution of HCl, the solution is dried over Na2SO4
  7. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-18bf7a45a4894d4ca2d0708043cae54b
Source dataset
uspto-grants-1980_01
Patent number
US04183951

Linked notes

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