Nitric Acid → Acetic acid 7-benzyloxy-6-nitro-1,2,3,4-tetrahydronaphthalen-2-yl ester

HRID 643904

Reaktionsgleichung

Reaktionsgleichung von HRID 643904
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([O:19][C:20](=[O:22])[CH3:21])[CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:23]([O-])([OH:25])=[O:24]>CC(O)=O.OS(O)(=O)=O.O.[N+]([O-])([O-])=O.[Cu+2].O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([O:19][C:20](=[O:22])[CH3:21])[CH2:16]2)=[CH:11][C:10]=1[N+:23]([O-:25])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 2

HCID 944Nitric AcidHCID 66750626Acetic acid 7-benzyloxy-1,2,3,4-tetrahydronaphthalen-2-yl ester

Produkt 1

HCID 66750447Acetic acid 7-benzyloxy-6-nitro-1,2,3,4-tetrahydronaphthalen-2-yl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1118Sulfuric AcidKatalysatorHCID 167780Copper(II) nitrate hemipentahydrateKatalysatorHCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

To a solution of acetic acid 7-benzyloxy-1,2,3,4-tetrahydronaphthalen-2-yl ester (5.77 g, 19.5 mmol) in AcOH (30 mL) is added a solution of 90% HNO3 (3.0 mL, ca. 64 mmol) in AcOH (5 mL), copper(II) nitrate hemipentahydrate (3.71 g, 19.8 mmol) and conc. H2SO4 (3 drops) at room temperature. The mixture is stirred at room temperature for 1.5 h and partitioned between EtOAc and aq. KOH. The organic layer is dried over MgSO4, concentrated and chromatographed to afford acetic acid 7-benzyloxy-6-nitro-1,2,3,4-tetrahydronaphthalen-2-yl ester with some impurities. Crystallization from DCM-hexanes yields a precipitate, which is quickly rinsed with Et2O-hexanes to afford pure acetic acid 7-benzyloxy-6-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl ester: 1H NMR (CDCl3) δ 7.66 (s, 1H), 7.48-7.29 (m, 5H), 6.80 (s, 1H), 5.22-5.15 (m, 1H), 5.19 (s, 2H), 3.10 (dd, J=16.0, 8.0 Hz, 1H), 2.95-2.72 (m, 3H), 2.05 (s, 3H), 2.05-1.95 (m, 2H).

Aufarbeitung

  1. custompartitioned between EtOAc and aq. KOH
  2. dry with materialThe organic layer is dried over MgSO4
  3. concentrationconcentrated
  4. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-10a7cfaa50044216a5f6aa06487b5c1a
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700633B2

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