Nitric Acid → 7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran

HRID 2292483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2292483
[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17].CCCCCC>C(O)(=O)C>[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N+:16]([O-:18])=[O:17])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 8058HexaneHCID 11805831HCID 11805831, Verbindung

Produkt 1

HCID 107531427-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
24 °C

Versuchsvorschrift

A solution of 7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan (10.0 g, 49.0 mmol) in glacial acetic acid 80 mL) is treated with 70% nitric acid (4.0 mL, 63.7 mmol) dropwise, and allowed to stir at 24° C. for 4 h. TLC (hexane) is used to monitor reaction progress. The reaction mixture is partitioned between Et2O (100 mL) and H2O (100 mL). The Et2O layer is washed with H2O (50 mL) and saturated Na2 CO3 (50 mL), dried (MgSO4), filtered and evaporated to a red solid (9.12 g). Crystallization from hexane provides 7-tert-butyl-3,3-dimethyl-5-nitro-2,3-dihydrobenzo[b]furan as an orange solid.

Aufarbeitung

  1. customreaction progress
  2. customThe reaction mixture is partitioned between Et2O (100 mL) and H2O (100 mL)
  3. washThe Et2O layer is washed with H2O (50 mL) and saturated Na2 CO3 (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to a red solid (9.12 g)
  7. customCrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-f6ad421a5c99424eb18fbb7e820671a8
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05684002

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