Potassium Carbonate → 4-(1,1-Dimethylpropyl)-benzenethiol

HRID 1670521Notes

Reaction equation

HRID 1670521 reaction equation
CN(C)C([S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:16])([CH3:15])[CH2:13][CH3:14])=[CH:8][CH:7]=1)=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:16][C:12]([C:9]1[CH:8]=[CH:7][C:6]([SH:5])=[CH:11][CH:10]=1)([CH3:15])[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 598223091-Dimethylcarbamoylthio-4-(1,1-dimethyl-propyl)-benzene

Product 1

HCID 151982394-(1,1-Dimethylpropyl)-benzenethiolYield 26.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reflux a mixture of 1-dimethylcarbamoylthio-4-(1,1-dimethyl-propyl)-benzene (520 mg, 2.1 mmol) and K2CO3 (1.28 g, 9.3 mmol) in methanol (40 mL) for 6 h. Cool to room temperature and concentrate in vacuo. Suspend the residue in water and acidify to pH 1 with 1M aqueous HCl. Extract the aqueous phase with EtOAc (3×40 mL). Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 97:3) to obtain the title compound (100 mg, 26%).

Workup

  1. temperatureReflux
  2. concentrationconcentrate in vacuo
  3. extractionExtract the aqueous phase with EtOAc (3×40 mL)
  4. dry with materialDry the combined organic extracts over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 97:3)

Sources & evidence

ORD record
ord-451c8419a6c8423e8db4ecb856fa01f0
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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