Water → 2,6-Bis(1,1-dimethylethyl)-4-(pentylthio)phenol

HRID 231587Notes

Reaction equation

HRID 231587 reaction equation
[O-]CC.[Na+].[CH3:5][C:6]([C:9]1[CH:14]=[C:13]([SH:15])[CH:12]=[C:11]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:10]=1[OH:20])([CH3:8])[CH3:7].Cl[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>C(O)C>[CH3:17][C:16]([C:11]1[CH:12]=[C:13]([S:15][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:14]=[C:9]([C:6]([CH3:5])([CH3:7])[CH3:8])[C:10]=1[OH:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 109771-ChloropentaneHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 2723922Sodium ethoxide

Product 1

HCID 144799502,6-Bis(1,1-dimethylethyl)-4-(pentylthio)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of freshly prepared sodium ethoxide (ca. 17 mmole) in ethanol (12 ml) was added with stirring 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (4.0 g, 17 mmole). After one hour, 1-chloropentane (4 ml, ca. 34 mmole) was added and the reaction mixture was stirred at room temperature for 20 hours. Water was added, and the mixture was extracted with diethyl ether. The ether layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to an oil. Chromatography on silica gel and recrystallization from pentane gave the title compound, m.p. 54°-55°.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialThe ether layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to an oil
  5. customChromatography on silica gel and recrystallization from pentane

Sources & evidence

ORD record
ord-648968c9808548d983e5033075bf2f32
Source dataset
uspto-grants-1989_07
Patent number
US04847305

Reaction notes

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