Formaldehyde → 2-(4-Methoxycarbonyl-2-nitrophenyl)propanol

HRID 2095230

Reaktionsgleichung

Reaktionsgleichung von HRID 2095230
CO[C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.[CH2:16]=[O:17].C[C:19](C)([O-:21])C.[K+]>CS(C)=O>[CH3:16][O:17][C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:11])[CH2:19][OH:21])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1)=[O:15]

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 21938352Methyl 4-ethyl-3-nitrobenzoateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 684541792-(4-Methoxycarbonyl-2-nitrophenyl)propanolAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a suspension of 4-ethyl-3-nitrobenzoic acid methyl ester (11d) (10 g, 48 mmol) and paraformaldehyde (1.8 g, 60 mmol) in DMSO (10 mL) was added in portions potassium tert-butoxide (1.46 g, 12 mmol), during which the colour of the reaction mixture was changing from yellow to purple. After stirring for 2.5 hours at room temperature, the reaction mixture was directly applied to the silica gel bed of a chromatography column (100 g silica, 3.5×14 cm) and eluted with hexane/ethyl acetate (EA) (3:1, v/v). The slightly yellow product (4d) was obtained in 38% yield (4.42 g, 18 mmol). Rf=0.24 (hexanes/EtOAc 7:3). 1H NMR (250 MHz, CDCl3) δ 8.36 (d, 1H, arom. H(3)), 8.18 (dd, 1H, arom. H(5)), 7.58 (d, 1H, arom. H(6)), 3.93 (s, 3H, COOCH3), 3.78 (m, 2H, α-CH2), 3.54 (sextet, 1H, β-CH), 1.69 (d, 3H, CH3).

Aufarbeitung

  1. washeluted with hexane/ethyl acetate (EA) (3:1

Quellen und Nachweise

ORD-Eintrag
ord-e63b3aa471a947daa96ab680cb18d9fb
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445734B2

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