Water → Ethanethiol, 2-(phenylmethoxy)-

HRID 1585657Notes

Reaction equation

HRID 1585657 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC(N)=[S:14].[OH-].[K+].O>C(O)C>[CH2:1]([O:8][CH2:9][CH2:10][SH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 223538Benzyl 2-Chloroethyl EtherHCID 2723790Thiourea

Product 1

HCID 14571805Ethanethiol, 2-(phenylmethoxy)-Yield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-benzyloxy-1-chloroethane (Synthesis, 1990, 495.) (7.2 g, 0.043 mol) and thiourea (3.2 g; 0.043 mol) in 95% ethanol (50 ml) was refluxed for 24 hours. To the reaction mixture, potassium hydroxide (4 g, 0.061 mol) and water (40 ml) were added and they were refluxed for 5 hours. The solvent was then distilled off under reduced pressure. The residue was neutralized with a 10% aqueous solution of sulfuric acid, followed by extraction with ethyl ether. The ether solution was washed with water, dried over sodium sulfate and then distilled off under reduced pressure, whereby 2-benzyloxyethanethiol (4.2 g, yield: 59.0%) was obtained as a colorless oil.

Workup

  1. temperaturethey were refluxed for 5 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. extractionfollowed by extraction with ethyl ether
  4. washThe ether solution was washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled off under reduced pressure

Sources & evidence

ORD record
ord-41d32e87700c4f76bad6b588c6f1ba84
Source dataset
uspto-grants-1999_08
Patent number
US05939448

Reaction notes

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