2-Bromopropane → HCID 14479951, compound

HRID 231588Notes

Reaction equation

HRID 231588 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])[CH3:3].[OH-].[Na+].Br[CH:20]([CH3:22])[CH3:21]>CC(C)=O>[CH3:13][C:12]([C:7]1[CH:8]=[C:9]([S:11][CH:20]([CH3:22])[CH3:21])[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:6]=1[OH:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 14798Sodium Hydroxide2×HCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

HCID 14479951HCID 14479951, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (2.0 g, 8.4 mmole) in acetone (20 ml) was added sodium hydroxide (0.71 g, 17.6 mmole). After the sodium hydroxide had reacted, 2-bromopropane (1.08 g, 8.8 mmole) was added, and the reaction mixture was stirred for two hours. The mixture was concentrated in vacuo to an oil that was dissolved in diethyl ether (50 ml), washed with water (30 ml in two portions), dried over sodium sulfate, filtered, and concentrated in vacuo to a solid. Chromatography on silica gel and recrystallization from aqueous methanol gave the title compound, m.p. 80°-82°.

Workup

  1. concentrationThe mixture was concentrated in vacuo to an oil that
  2. dissolutionwas dissolved in diethyl ether (50 ml)
  3. washwashed with water (30 ml in two portions)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a solid
  7. customChromatography on silica gel and recrystallization from aqueous methanol

Sources & evidence

ORD record
ord-89406738426a4a70aa5aa9074378fb8d
Source dataset
uspto-grants-1989_07
Patent number
US04847305

Reaction notes

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