4-tert-Pentylphenol → HCID 59822306, compound

HRID 1670520Notes

Reaction equation

HRID 1670520 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][CH3:4].[CH3:13][N:14]([CH3:18])[C:15](Cl)=[S:16].C1N2CCN(CC2)C1>CN(C=O)C>[CH3:5][C:2]([C:6]1[CH:7]=[CH:8][C:9]([O:12][C:15](=[S:16])[N:14]([CH3:18])[CH3:13])=[CH:10][CH:11]=1)([CH3:1])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 66434-tert-PentylphenolHCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chloride

Product 1

HCID 59822306HCID 59822306, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir a mixture of 4-(1,1-dimethyl-propyl)-phenol (1.96 g, 11.9 mmol), N,N-dimethylthiocarbamoyl chloride (2.94 g, 23.8 mmol) and DABCO (2.82 g, 25.1 mmol) in anhydrous DMF (30 mL) at room temperature for 16 h under a nitrogen atmosphere. Pour reaction onto ice and extract the mixture with EtOAc (3×75 mL). Combine the organic extracts and wash with 0.5 M aqueous HCl. Dry the organic phase over MgSO4 and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain the desired intermediate as a yellow solid (2.28 g, 76%). MS (ES+) m/z: 252.3 (M+H)+.

Workup

  1. additionPour
  2. customreaction onto ice
  3. extractionextract the mixture with EtOAc (3×75 mL)
  4. washCombine the organic extracts and wash with 0.5 M aqueous HCl
  5. dry with materialDry the organic phase over MgSO4
  6. concentrationconcentrate in vacuo
  7. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-b92a29b4be8c4742989e392aaa28e015
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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