tert-Butanol → 2-tert-Butyl-4-(2-methylbutan-2-yl)phenol

HRID 258209

반응식

HRID 258209 반응식
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[C:13](O)([CH3:16])([CH3:15])[CH3:14].[OH-].[Na+]>FC(F)(F)C(O)=O>[C:1]([C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:11]=1)([CH2:4][CH3:5])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 6386tert-ButanolHCID 66434-tert-PentylphenolHCID 14798Sodium Hydroxide

생성물 1

HCID 147658522-tert-Butyl-4-(2-methylbutan-2-yl)phenol수율 39%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

4-t-amylphenol (80 g, 0.49 mole) was dissolved in 200 ml anhydrous trifluoroacetic acid (TFA). T-butyl alcohol (39 g, 0.53 mole) was added with stirring. The mixture was stoppered and stirred for 19 hours at ambient (~22° C.) temperature. The solution was then poured into 400 ml of 1M NaOH, and the resulting upper organic layer was isolated in a separatory funnel. The crude product was dried over anhydrous magnesium sulfate. The product, 4-t-amyl-2-t-butylphenol, was purified by eluting 35 g of the mixture 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)) were combined and rotoevaporated to a thick syrup. The yield was 39%.

후처리

  1. stirringstirred for 19 hours at ambient (~22° C.) temperature
  2. customthe resulting upper organic layer was isolated in a separatory funnel
  3. dry with materialThe crude product was dried over anhydrous magnesium sulfate
  4. customThe product, 4-t-amyl-2-t-butylphenol, was purified
  5. washby eluting 35 g of the mixture 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. washby Thin Layer Chromatography (TLC) (on silica eluted with 60:40 hexanes:dichloromethane (v/v))

출처 및 근거

ORD 기록
ord-411ba83f4e034518b70d58ca1f1cb3ab
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05266283

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