Aluminium lithium hydride → 2,3,6-Trimethyl-4-sulfanylphenol

HRID 2102986Notes

Reaction equation

HRID 2102986 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([S:9]C#N)[CH:5]=[C:4]([CH3:12])[C:3]=1[OH:13].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[SH:9][C:6]1[CH:5]=[C:4]([CH3:12])[C:3]([OH:13])=[C:2]([CH3:1])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 235038182,3,6-Trimethyl-4-thiocyanato-phenol

Product 1

HCID 157080962,3,6-Trimethyl-4-sulfanylphenolYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2,3,6-trimethyl-4-thiocyanato-phenol (45.7 g, 237 mmol) in anhydrous THF (300 mL) was added to a suspension of LiAlH4 (9.09 g) in anhydrous THF (600 mL) stirred at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 15 h. It was subsequently quenched with THF, followed by H2O and 0.5 M aq. HCl. Extraction with EtOAc (3×) was followed by washing the collected organic fractions with brine, drying over Na2SO4 and solvent evaporation. Column chromatography (SiO2: hexane:EtOAc, 9:1 v/v) yielded 4-mercapto-2,3,6-trimethyl-phenol as a white solid (32 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 15 h
  3. customIt was subsequently quenched with THF
  4. extractionExtraction with EtOAc (3×)
  5. washby washing the collected organic fractions with brine
  6. dry with materialdrying over Na2SO4 and solvent evaporation

Sources & evidence

ORD record
ord-04274b18dea149948c39b76d77cb83cf
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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