tert-Butanol → Tert-butyl 4-methyl-3-nitrobenzoate

HRID 381309

Reaktionsgleichung

Reaktionsgleichung von HRID 381309
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[C:14](O)([CH3:17])([CH3:16])[CH3:15].Cl.CN(C)CCCN=C=NCC.C(OCC)(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[C:14]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:12]([CH3:13])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:17])([CH3:16])[CH3:15]

Komponenten

7

Edukt 4

HCID 6386tert-ButanolHCID 73194-Methyl-3-nitrobenzoic acidHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 22451886Tert-butyl 4-methyl-3-nitrobenzoateAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-nitro-4-methylbenzoic acid (17.3 g 96 mmol) in dichloromethane (250 ml) and tert-butanol (35.8 g 470 mmol) at 0° C. under nitrogen was added 4-dimethylaminopyridine (6 g 50 mmol) and 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (25.8 g 140 mmol) and the solution allowed to come to room temperature over 1 hour. then stirred overnight. The solution was poured into 1:1 ethyl acetate:water (800 ml) and the organic layer washed with aqueous bicarbonate and saturated aqueous sodium chloride. then dried (MgSO4) and evaporated. to give the product as a clear oil (22.6 g).

Aufarbeitung

  1. washwater (800 ml) and the organic layer washed with aqueous bicarbonate and saturated aqueous sodium chloride
  2. dry with materialthen dried (MgSO4)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5954dda2b21e4891a6aa88f0d3e45ef0
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306852B1

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