Sulfuric Acid → HCID 73882372, compound

HRID 498140

Reaction equation

HRID 498140 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 73882372HCID 73882372, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b3cd28d7bbf749c69f5d3ff833507ba3
Source dataset
uspto-grants-2005_09
Patent number
US06949678B2

Linked notes

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