Sulfuric Acid → HCID 73882372、化合物

HRID 130634

反応式

HRID 130634 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 73882372HCID 73882372、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3c79590acae74f1b950b0ce2cc130ffe
出典データセット
uspto-grants-2008_06
特許番号
US07381842B2

関連ノート

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