tert-Butanol → Tert-butyl 4-cyanobenzoate

HRID 979774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 979774
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].[C:12](O)([CH3:15])([CH3:14])[CH3:13].Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CN(C)C1C=CN=CC=1>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Komponenten

6

Edukt 3

HCID 6386tert-ButanolHCID 120874-Cyanobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 271408Tert-butyl 4-cyanobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Dissolve 22.1 g 4-cyanobenzoic acid and 28.2 ml t-butanol in 500 ml DMF. Add 9.15 g 4-(dimethylamino) pyridine and 31.5 g 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. Stir the mixture overnight at RT. Remove the DMF in vacuo, and partition the resultant residue between ethyl acetate and water. Wash the organic layer successively with cold 0.5 N aqueous HCl, water, 5% aqueous NaHC03 and brine. Dry the organic layer over MgSO4 and evaporate the solvent to obtain the title compound. m.p. 75°-78° C. Rf (silica gel; 5% EtOAc in hexane)=0.3; IR 2240 cm-1 ; 1730 cm-1.

Aufarbeitung

  1. customRemove the DMF in vacuo
  2. custompartition the resultant residue between ethyl acetate and water
  3. washWash the organic layer successively with cold 0.5 N aqueous HCl, water, 5% aqueous NaHC03 and brine
  4. dry with materialDry the organic layer over MgSO4
  5. customevaporate the solvent

Quellen und Nachweise

ORD-Eintrag
ord-3a3d30f66e2a4a77b8d2ec22ad808e8f
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04634689

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