Water → 1,3-Bis(1,1-dimethylethyl)-2-methoxy-5-(methylthio)benzene

HRID 231591Notes

Reaction equation

HRID 231591 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]=1[OH:17])([CH3:4])[CH3:3].[OH-].[Na+].[CH3:20]I.O>CN(C)C=O>[CH3:14][C:13]([C:7]1[CH:8]=[C:9]([S:11][CH3:12])[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:6]=1[O:17][CH3:20])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 144799522,6-Bis(1,1-dimethylethyl)-4-(methylthio)phenol

Product 1

HCID 144799541,3-Bis(1,1-dimethylethyl)-2-methoxy-5-(methylthio)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-bis(1,1-dimethylethyl)-4-(methylthio)phenol (1.16 g, 4.6 mmole) in dimethylformamide (15 ml) was added sodium hydroxide (0.37 g, 9.2 mmole). After the solution was warmed for one hour, methyl iodide (0.72 g, 5.1 mmole) was added, and the mixture was warmed for an additional three hours. The reaction mixture was poured into water (150 ml) and extracted with diethyl ether (180 ml in three positions). The ether extract was washed with saturated aqueous sodium carbonate, dried over sodium sulfate, filtered, and concentrated in vacuo to an oil. Upon standing the oil crystallized. Recrystallization from hexane gave the title compound, m.p. 50°-52°.

Workup

  1. temperatureAfter the solution was warmed for one hour
  2. temperaturethe mixture was warmed for an additional three hours
  3. extractionextracted with diethyl ether (180 ml in three positions)
  4. extractionThe ether extract
  5. washwas washed with saturated aqueous sodium carbonate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to an oil
  9. customcrystallized
  10. customRecrystallization from hexane

Sources & evidence

ORD record
ord-3e4d096df26a45e0b3567a40b3af992d
Source dataset
uspto-grants-1989_07
Patent number
US04847305

Reaction notes

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