2-Methyl-2-butanol → HCID 15173853, compound

HRID 258215Notes

Reaction equation

HRID 258215 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:12](O)([CH2:15][CH3:16])([CH3:14])[CH3:13].[OH-].[Na+]>FC(F)(F)C(O)=O>[C:12]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=[CH:7][C:8]=1[OH:11])([CH2:15][CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 64052-Methyl-2-butanolHCID 73934-tert-ButylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 15173853HCID 15173853, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-t-butylphenol (73 g, 0.49 mole) is dissolved in 200 ml anhydrous trifluoroacetic acid (TFA). T-amyl alcohol (47 g, 0.53 mole) is added with stirring. The mixture is stoppered and stirred for 19 hours at ambient (~22° C.) temperature. The solution is then diluted into 400 ml of 1M NaOH, and the resulting upper organic layer is isolated in a separatory funnel. The crude product is dried over anhydrous magnesium sulfate. The product, 2-t-amyl-4-t-butylphenol, is purified by eluting 35 g of the mixture with 60:40 hexanes:dichloromethane (v/v) in a 5×20 cm silica column and eluted with 300 to 700 ml of solvent and collected in aliquots of 50 ml. Aliquots showing a single spot by Thin Layer Chromatography (TLC) (on silica eluted with 60:40 hexanes:dichloromethane v/v)) are combined and rotoevaporated to a thick syrup, typically giving a 40% yield.

Workup

  1. stirringstirred for 19 hours at ambient (~22° C.) temperature
  2. customthe resulting upper organic layer is isolated in a separatory funnel
  3. dry with materialThe crude product is dried over anhydrous magnesium sulfate
  4. customThe product, 2-t-amyl-4-t-butylphenol, is purified
  5. washby eluting 35 g of the mixture with 60:40 hexanes
  6. washdichloromethane (v/v) in a 5×20 cm silica column and eluted with 300 to 700 ml of solvent
  7. customcollected in aliquots of 50 ml
  8. washeluted with 60:40 hexanes
  9. customtypically giving a 40% yield

Sources & evidence

ORD record
ord-8b4019c925614f35998b12aa5eceff19
Source dataset
uspto-grants-1993_11
Patent number
US05266283

Reaction notes

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