Water → Ethanethiol, 2-(phenylmethoxy)-

HRID 1108038Notes

Reaction equation

HRID 1108038 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-f589a9af5d1044a28a6f76dd46691238
Source dataset
uspto-grants-2000_05
Patent number
US06063945

Reaction notes

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