Sulfuric Acid → Tert-butyl 4-cyanobenzoate

HRID 1417185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1417185
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].S(=O)(=O)(O)O.[CH2:17]=[C:18]([CH3:20])[CH3:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:18]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)([CH3:20])([CH3:19])[CH3:17]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 120874-Cyanobenzoic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 271408Tert-butyl 4-cyanobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In 612 ml of methylene chloride was suspended 45.0 g of 4-cyanobenzoic acid and 3.1 ml of conc. sulfuric acid. To the suspension was added, while stirring at 0° C., 310 ml of isobutene. The mixture was stirred for 13 days. The reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The resulting precipitate was collected by filtration and washed with hexane. The filtrate and the washings were combined and concentrated under reduced pressure. The concentrate was purified by silica gel chromatography (hexane/ethyl acetate=10/1), followed by crystallization from methylene chloride/petroleum ether to afford 43.1 g of the title compound as a white crystalline product.

Aufarbeitung

  1. additionTo the suspension was added
  2. stirringThe mixture was stirred for 13 days
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with hexane
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate was purified by silica gel chromatography (hexane/ethyl acetate=10/1)
  9. customfollowed by crystallization from methylene chloride/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-8d773e051128425d8a4e75220f723c49
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05876756

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