4-Nitrophenol → Ethyl 2-(4-nitrophenoxy)acetate

HRID 54980

Reaktionsgleichung

Reaktionsgleichung von HRID 54980
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].C(#N)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 9804-NitrophenolHCID 7751Ethyl chloroacetateHCID 11430Potassium Carbonate

Produkt 1

HCID 308938Ethyl 2-(4-nitrophenoxy)acetateAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The product was made by procedures which are well known in the art, that is, by alkylation of 4-nitrophenol (29.2 g, 0.21 mol) with ethyl chloroacetate (24.5 g, 0.20 mole) in the presence of potassium carbonate (30.4 g, 0.22 mol), potassium iodide (0.5 g) and acetonitrile (150 mL) to afford ethyl 4-nitrophenoxyacetate (33 g, 73.3%), m.p. 75°-76° C. after recrystallization from tert-butylmethyl ether; hydrogenation of the latter (22.5 g) at 50 psi in ethyl acetate (200 mL) in the presence of 10% palladium on Carbon (0.3 g) to afford 22.5 g (97%) of ethyl 4-aminophenoxyacetate, m.p. 157°-158° C.; and treatment of the latter (18.52 g, 0.08 mol) with methanesulfonyl chloride (12.6 g, 0.11 mol) in CH2Cl2 (250 mL) in the presence of pyridine (35 mL) to afford N-[4-(ethoxycarbonylmethoxy)phenyl]methanesulfonamide, 20.06 g (92%), m.p. 77.3°-78.5° C. after recrystallization from ethanol.

Quellen und Nachweise

ORD-Eintrag
ord-8ca84b6c8a5f4c9ea78b35e1dc641c25
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624922

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