Sodium Hydroxide → HCID 10989866, compound

HRID 263088Notes

Reaction equation

HRID 263088 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1.[OH-].[Na+]>C(O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 660494-BromothiophenolHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 10989866HCID 10989866, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 30 g (0.165 mol) of ethyl 2-bromopropionate in 30 ml of anhydrous ethanol is run over the course of 30 minutes into a solution of 29 g (0.150 mol) of p-bromothiophenol, taken as 98% strength, and of 6 g (0.150 mol) of sodium hydroxide pellets in 100 ml of anhydrous ethanol, and the mixture is then stirred for 1 hour at ambient temperature. The inorganic salts formed are removed by filtration and the alcohol is evaporated. The residue is taken up in diethyl ether and the organic phase obtained is washed successively with N sodium hydroxide solution and with water. After drying, and evaporating the solvent, 44.6 g of a limpid pale yellow oil are obtained. The purification of this oil by distillation under reduced pressure gives 37.1 g of a limpid colourless oil.

Workup

  1. customThe inorganic salts formed
  2. customare removed by filtration
  3. customthe alcohol is evaporated
  4. customthe organic phase obtained
  5. washis washed successively with N sodium hydroxide solution and with water
  6. customAfter drying
  7. customevaporating the solvent, 44.6 g of a limpid pale yellow oil
  8. customare obtained
  9. customThe purification of this oil
  10. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-62ebe1e0c57645baafbd16a1fc835e30
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

Loading…