Acetic Anhydride → S-(3-Methoxyphenyl) ethanethioate

HRID 410034Notes

Reaction equation

HRID 410034 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[CH3:10][C:11](OC(C)=O)=[O:12]>C(Cl)Cl>[C:11](=[O:12])([S:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 849893-Methoxybenzenethiol

Product 1

HCID 539677S-(3-Methoxyphenyl) ethanethioateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxybenzenethiol (5 g, 35.66 mmol) and TEA (7.45 ml, 53.49 mmol) in DCM (60 ml) was added Ac2O (4 g, 39.23 mmol) at room temperature and stirred for 3 hours. The reaction mixture was washed with 1 N HCl (50 ml×2), water (50 ml×2) and brine (50 ml), dried with anhydrous sodium sulfate, filtered and concentrated to afford product as a yellow solid (6.5 g, 100%). MS (ESI): m/z 183.1 [M+1]+.

Workup

  1. washThe reaction mixture was washed with 1 N HCl (50 ml×2), water (50 ml×2) and brine (50 ml)
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-45126fe8e6994ae18244c1db83c0ba06
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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