Phenol → 1-(2-Methoxy-4-nitrophenoxy)-2-methylpropan-2-ol

HRID 1916350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916350
[K].[CH3:2][O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13].[CH3:14][C:15]1([O:18][CH2:17]1)[CH3:16].C1(O)C=CC=CC=1>O.CC#N>[CH3:2][O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:13][CH2:14][C:15]([CH3:17])([OH:18])[CH3:16]

Komponenten

6

Edukt 4

HCID 996PhenolHCID 11208Isobutylene oxideHCID 767382-Methoxy-4-nitrophenolHCID 5462222Potassium

Produkt 1

HCID 588580781-(2-Methoxy-4-nitrophenoxy)-2-methylpropan-2-olAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A steel bomb, fitted with an internal thermocouple, pressure gauge and safety release valve rated at 3000 psi, with ˜55 mL capacity was charged with the potassium salt of 2-methoxy-4-nitrophenol (6 g, 29 mmol), NaH2PO4 (3.3 g, 27.7 mmol), isobutylene oxide (2.8 g, 35 mmol) and 30 mL of 15% H2O/MeCN. The sealed bomb was heated at 170° C. for three hr. Following cooling, HPLC revealed all starting phenol had been converted to product. The biphasic solution was concentrated using a rotary evaporator before being partitioned between CH2Cl2 and H2O. The aqueous phase was extracted 3× with CH2Cl2; the combined CH2Cl2 fractions were washed 3× with aq KHCO3/K2CO3 and once with H2O. After drying over Na2SO4, concentration under vacuum yielded 6.9 g of desired product as a tan solid.

Aufarbeitung

  1. temperatureFollowing cooling
  2. concentrationThe biphasic solution was concentrated
  3. customa rotary evaporator
  4. custombefore being partitioned between CH2Cl2 and H2O
  5. extractionThe aqueous phase was extracted 3× with CH2Cl2
  6. washthe combined CH2Cl2 fractions were washed 3× with aq KHCO3/K2CO3
  7. dry with materialAfter drying over Na2SO4, concentration under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-373f42e96e124b13b780cf9ee2a386c2
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618115B2

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