Hydrochloric Acid → 4'-tert-Butyl-2,6-dimethyl-biphenyl-4-thiol

HRID 1157743Notes

Reaction equation

HRID 1157743 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([S:18]C(=O)N(C)C)=[CH:13][C:12]=2[CH3:24])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].Cl>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([CH3:24])=[CH:13][C:14]([SH:18])=[CH:15][C:16]=2[CH3:17])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86625172dimethyl-thiocarbamic acid S-(4'-tert-butyl-2,6-dimethyl-biphenyl-4-yl) ester

Product 1

HCID 593560484'-tert-Butyl-2,6-dimethyl-biphenyl-4-thiolYield 83.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of dimethyl-thiocarbamic acid S-(4′-tert-butyl-2,6-dimethyl-biphenyl-4-yl) ester (8.8 g, 25.8 mmol) in methanol (65 mL) is added sodium methoxide (1.39 g, 25.8 mmol). The reaction mixture is heated to reflux overnight. After cooling to room temperature, the reaction mixture is neutralized with 5N HCl, concentrated to ⅓ volume, treated with brine, and extracted into dichloromethane. The aqueous layer is back-extracted with dichloromethane, and the combined organic layers are dried and concentrated. The resulting residue is applied to silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 50% to give the title compound (5.84 g).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. additiontreated with brine
  5. extractionextracted into dichloromethane
  6. extractionThe aqueous layer is back-extracted with dichloromethane
  7. customthe combined organic layers are dried
  8. concentrationconcentrated
  9. washeluted

Sources & evidence

ORD record
ord-80d5f6cf6e7c491fb9c98e40707eaf38
Source dataset
uspto-grants-2010_10
Patent number
US07807702B2

Reaction notes

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