1-Hexanethiol → HCID 23365679, compound

HRID 1080705Notes

Reaction equation

HRID 1080705 reaction equation
CO[CH:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[CH2:18]([SH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C(Cl)Cl.S(=O)(=O)(O)O>[CH2:18]([S:24][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 81061-HexanethiolHCID 12957105HCID 12957105, compound

Product 1

HCID 23365679HCID 23365679, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl α-methoxy-3,4-dimethoxyphenylacetate (0.39 g) in methylene chloride (5 ml) were added hexanethiol (0.35 ml) and 3 drops of concentrated sulfuric acid and the mixture was stirred for 30 minutes. Then it was washed with water and brine, dried (magnesium sulfate) and evaporated to give an oily residue. Purification by column chromatography on silica gel with elution by 1:9 ethyl acetate-hexane provided methyl α-hexylthio-3,4-dimethoxyphenylacetate (0.37 g), a compound of Formula 4 wherein X is S, R5 is 3,4-dimethoxyphenyl and R7 is hexyl.

Workup

  1. washThen it was washed with water and brine
  2. dry with materialdried (magnesium sulfate)
  3. customevaporated
  4. customto give an oily residue
  5. customPurification by column chromatography on silica gel
  6. washwith elution by 1:9 ethyl acetate-hexane

Sources & evidence

ORD record
ord-fd919b0274474b50895287a59716c99a
Source dataset
uspto-grants-1996_12
Patent number
US05583147

Reaction notes

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