4-Methylbenzenethiol → HCID 58442533, compound

HRID 1465651Notes

Reaction equation

HRID 1465651 reaction equation
I[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][CH:15]=1.[OH-].[K+]>CN(C=O)C.O.[Cu-]=O>[CH3:8][C:6]1[CH:7]=[C:2]([S:20][C:17]2[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=2)[CH:3]=[C:4]([CH3:12])[C:5]=1[C:9](=[O:11])[CH3:10]

Participants

7

Reactant 3

HCID 78114-MethylbenzenethiolHCID 14797Potassium HydroxideHCID 58442513HCID 58442513, compound

Product 1

HCID 58442533HCID 58442533, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-iodo-2,6-dimethylphenyl)ethanone (1.5 g, 5.5 mmol, 1.0 equiv), 4-methylbenzenethiol (1.02 g, 8.2 mmol, 1.5 equiv), copper(I) oxide (39.2 mg, 0.3 mmol, 0.05 equiv), and potassium hydroxide (614.1 mg, 11.0 mmol, 2.0 equiv) in DMF (4.4 mL) and H2O (1.1 mL) was heated at reflux for 20 h. The mixture was quenched with H2O (10 mL) and extracted with ether (2×20 mL). The organic layer was collected, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (3.0% EtOAc in hexanes as eluant) to provide 1-(2,6-dimethyl-4-(p-tolylthio)phenyl)ethanone (1.16 g, 4.3 mmol) as yellow oil in 79% yield: 1H NMR (CD3OD, 500 MHz) δ 7.29 (d, J=8.0 Hz, 2 H), 7.20 (d, J=8.0 Hz, 2 H), 6.88 (s, 2 H), 2.45 (s, 3 H), 2.35 (s, 3 H), 2.15 (s, 6 H); ESI-MS: m/z 271.8 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. customThe mixture was quenched with H2O (10 mL)
  4. extractionextracted with ether (2×20 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over MgSO4(s)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (3.0% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-313117db6d43439d943c6eee618ee814
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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