Ammonia → (4-Allyloxy-2-methyl-phenyl)-methanethiol

HRID 892258Notes

Reaction equation

HRID 892258 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](CCl)=[CH:7][C:6]=1C)[CH:2]=[CH2:3].N[C:15](N)=[S:16].O.N.[CH2:20](O)C>>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:15][SH:16])=[C:9]([CH3:20])[CH:10]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 702Ethanol2×HCID 962WaterHCID 2723790ThioureaHCID 222420771-Allyloxy-4-chloromethyl-2-methyl-benzene

Product 1

HCID 22242072(4-Allyloxy-2-methyl-phenyl)-methanethiolYield 59%

Procedure

A mixture of 3.40 g (17.3 mmol) 1-allyloxy-4-chloromethyl-2-methyl-benzene and 1.45 g (19.0 mmol) thiourea in 5.0 ml ethanol was heated to reflux for 7 h. Solvents were distilled off and the crystalline residue was washed with cold ethanol and isolated by filtration. After addition of 5.0 ml ethanol, 2.0 ml water and 1.4 ml 25% aqueous ammonia, the mixture was heated to reflux for 2 h. Ethanol was distilled off, then acidified with 0.5 ml half conc. HCl and extracted with ethyl acetate. The solution was dried over MgSO4 and solvents were removed in vacuum to yield 1.99 g (59%) (4-allyloxy-2-methyl-phenyl)-methanethiol as nearly colourless oil, which was used immediately.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 h
  3. distillationSolvents were distilled off
  4. washthe crystalline residue was washed with cold ethanol
  5. customisolated by filtration
  6. temperaturethe mixture was heated
  7. temperatureto reflux for 2 h
  8. distillationEthanol was distilled off
  9. extractionextracted with ethyl acetate
  10. dry with materialThe solution was dried over MgSO4 and solvents
  11. customwere removed in vacuum

Sources & evidence

ORD record
ord-709ec8683c6b48afb89ef8834ce413d1
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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