D-1,4-Dithiothreitol → 5-tert-Butyl-4-mercapto-2-methyl-phenol

HRID 356507Notes

Reaction equation

HRID 356507 reaction equation
[C:1]([C:5]1[C:6]([S:13]C#N)=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].SC[C@H]([C@@H](CS)O)O.OP([O-])(O)=O.[K+]>CCO>[C:1]([C:5]1[C:6]([SH:13])=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 446094D-1,4-Dithiothreitol2×HCID 516951Monobasic potassium phosphate2×HCID 105609555-tert-Butyl-2-methyl-4-thiocyanato-phenol

Product 1

HCID 107030535-tert-Butyl-4-mercapto-2-methyl-phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round bottom flask equipped with a magnetic stirrer and condenser were added 35 g (158 mmol) of 5-tert-butyl-2-methyl-4-thiocyanato-phenol prepared in Example GGG, dithiothreitol (25.61 g, 166 mmol), EtOH (250 mL), and 0.02M KH2PO4 buffer solution (25 mL), respectively. The reaction was heated to reflux; after 2 hours, additional dithiothreitol (5.0 g, 32.4 mmol) and 0.02M KH2PO4 buffer solution (25 mL) were added. After 2 hours at reflux, the solution was cooled to room temperature and concentrated. The reaction was quenched with brine and extracted with 1:1 Et2O:hexanes. The organic layer was washed with brine, dried (MgSO4), and concentrated. The residue was submitted to column chromatography (100% CHCl3, silica gel) to yield the title compound. 1H NMR (CDCl3) δ 1.45 (s, 9 H), 2.15 (s, 3 H), 3.43 (s, 1 H), 4.56 (br s, 1 H), 6.82 (s, 1 H), 7.05 (s, 1 H).

Workup

  1. customTo a round bottom flask equipped with a magnetic stirrer and condenser
  2. temperatureThe reaction was heated to reflux
  3. temperatureAfter 2 hours at reflux
  4. concentrationconcentrated
  5. customThe reaction was quenched with brine
  6. extractionextracted with 1:1 Et2O
  7. washThe organic layer was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a51d6d9037e449c4ab3758f85f310ba2
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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