1-Dodecanethiol → HCID 129359612, compound

HRID 591500Notes

Reaction equation

HRID 591500 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(S)CCCCCCCCCCC.[CH3:18][O:19][C:20](=[O:34])[CH2:21][C:22]1[C:26]2[CH:27]=[CH:28][C:29]([O:32]C)=[C:30]([CH3:31])[C:25]=2[S:24][CH:23]=1>C1(C)C=CC=CC=1>[CH3:18][O:19][C:20](=[O:34])[CH2:21][C:22]1[C:26]2[CH:27]=[CH:28][C:29]([OH:32])=[C:30]([CH3:31])[C:25]=2[S:24][CH:23]=1

Participants

5

Reactant 3

HCID 81951-DodecanethiolHCID 6451240Aluminum(III) ChlorideHCID 131734521HCID 131734521, compound

Product 1

HCID 129359612HCID 129359612, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of aluminum chloride (3.30 g) and toluene (30 mL) was added 1-dodecanethiol (17.80 mL) at room temperature, and the mixture was stirred at room temperature for 30 min. To the mixture was added methyl(6-methoxy-7-methyl-1-benzothiophen-3-yl)acetate (3.1 g) at room temperature. The mixture was stirred at room temperature for 13 h. The mixture was quenched with ice water at 0° C. and extracted with EtOAc. The organic layer was separated, washed successively with 1N HCl and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (1.580 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 13 h
  2. customThe mixture was quenched with ice water at 0° C.
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed successively with 1N HCl and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-24394a4eef2042cf9b4906a8098d7fc9
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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