Sulfuric Acid → HCID 73882372, Verbindung

HRID 130634

Reaktionsgleichung

Reaktionsgleichung von HRID 130634
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:5][CH:4]=1.[N:22](OC)=[O:23].OS(O)(=O)=O.N([O-])=O.[Na+]>CO.O.C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13](=[O:21])[C:14](=[N:22][OH:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:5][CH:4]=1

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 12231Methyl nitriteHCID 223208401-(4-Methoxynaphthyl)-octan-1-oneHCID 23668193Sodium Nitrite

Produkt 1

HCID 73882372HCID 73882372, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

10.0 g (35.2 mmol) of 1-(4-methoxynaphthyl)-octan-1-one are dissolved in 35 mL of t-butyl methyl ether. HCl-gas is introduced into this solution under cooling in an ice bath, and methyl nitrite-gas, which is genarated by adding H2SO4 aq. solution (3.5 mL of conc. H2SO4 and 7 mL of H2O) into NaNO2 (3.65 g, 52.7 mmol) in methanol (3 mL) and H2O (3 mL), is introduced for 10 min at an ice-bath temperature. Then, the reaction solution is poured into ice, and the crude product is extracted with t-butyl methyl ether. This ether layer is washed with saturated NaHCO3 aq. solution and brine, dried over anhydrous MgSO4, and then condensed. The residue is applied to column chromatography on silica gel with ethyl acetate -hexane (10:90) as eluent. 2.02 g of yellow solid are obtained (18%). M.p. 92-93° C. 1H-NMR spectrum (CDCl3). δ [ppm]: 0.90 (t, 3H), 1.31-1.55 (m, 6H), 1.59-1.65 (m , 2H), 2.79 (t, 2H), 4.06 (s, 3H), 6.80 (d, 1H), 7.51 (t, 1H), 7.58 (t, 1H), 7.72 (d, 1H), 7.75 (d, 1H), 8.33 (d, 1H), 8.44 (d, 1H).

Aufarbeitung

  1. additionis introduced into this solution
  2. temperatureunder cooling in an ice bath
  3. additionis introduced for 10 min at an ice-bath temperature
  4. additionThen, the reaction solution is poured into ice
  5. extractionthe crude product is extracted with t-butyl methyl ether
  6. washThis ether layer is washed with saturated NaHCO3 aq. solution and brine
  7. dry with materialdried over anhydrous MgSO4
  8. customcondensed

Quellen und Nachweise

ORD-Eintrag
ord-3c79590acae74f1b950b0ce2cc130ffe
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381842B2

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