Hydrochloric Acid → 4-Tert-butyl-2-(1-hydroxy-2-methylpropan-2-yl)-5-nitrophenol

HRID 76781

Reaktionsgleichung

Reaktionsgleichung von HRID 76781
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[C:12]([N+:25]([O-:27])=[O:26])=[CH:13][C:14]([OH:24])=[C:15]([C:17]([CH3:23])([CH3:22])[C:18](OC)=[O:19])[CH:16]=1)([CH3:10])([CH3:9])[CH3:8].Cl>C1COCC1.CO>[C:7]([C:11]1[C:12]([N+:25]([O-:27])=[O:26])=[CH:13][C:14]([OH:24])=[C:15]([C:17]([CH3:23])([CH3:22])[CH2:18][OH:19])[CH:16]=1)([CH3:10])([CH3:8])[CH3:9]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 59544161Methyl 2-(5-tert-butyl-2-hydroxy-4-nitrophenyl)-2-methylpropanoate

Produkt 1

HCID 595441534-Tert-butyl-2-(1-hydroxy-2-methylpropan-2-yl)-5-nitrophenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A 1M solution of lithium aluminum hydride in THF (11.80 mL, 11.80 mmol) was added to a solution of methyl 2-(5-tert-butyl-2-hydroxy-4-nitrophenyl)-2-methylpropanoate (5.36 g, 18.15 mmol) in THF (50 mL). The mixture was stirred at ambient temperature for 3 h, and then diluted with methanol. The mixture was acidified with 1N HCl (pH 1-2) and the aqueous phase was extracted with MTBE. The organic phase was dried in vacuo to afford 4-tert-butyl-2-(1-hydroxy-2-methylpropan-2-yl)-5-nitrophenol which was used without further purification in the next step. 1H-NMR (400 MHZ, DMSO-d6) δ 10.12 (s, 1H); 7.37 (s, 1H); 6.80 (s, 1H); 4.77 (s, 1H); 3.69-3.65 (m, 2H); 1.30 (s, 9H); 1.29 (s, 6H)

Aufarbeitung

  1. extractionthe aqueous phase was extracted with MTBE
  2. customThe organic phase was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-81cdb1ee08cf4e818320445c607d55a1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835639B2

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