1-Methylcyclohexanecarboxylic acid → HCID 178421666、化合物

HRID 1737147ノート

反応式

HRID 1737147 の反応式
[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:14][C:15]1(C(O)=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.S(O[O-])([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.C(OCC)C.[N+]([O-])([O-])=O.[Ag+]>[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[C:11]=1[C:15]1([CH3:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[CH:8][CH:7]=[CH:6][CH:5]=2

参加物

8

反応物 3

HCID 707441-Methylcyclohexanecarboxylic acidHCID 9855511Ammonium peroxysulphateHCID 178516607HCID 178516607、化合物

生成物 1

HCID 178421666HCID 178421666、化合物収率 19.2%

試薬・触媒・溶媒 4

HCID 24470Silver Nitrate触媒HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
20 °C

実験手順

To a stirred solution of 2-hydroxy-naphthalene-1,4-dione (1.00 g, 5.7 mmol), 1-methylcyclohexanecarboxylic acid (1.22 g, 8.6 mmol) and silver nitrate (600 mg) in a mixture of acetonitrile (20 ml) and water (20 ml) at 65° C. was slowly added a solution of ammonium peroxysulphate (1.96 g, 8.6 mmol) in water (10 ml) over a period of 15 minutes. The mixture was heated for a further hour before cooling to room temperature (about 20° C.) and diluting with diethyl ether (50 ml). The organic phase was separated and washed successively with water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution before drying over magnesium sulphate. Filtration and evaporation of the solvent under reduced pressure followed by silica gel column chromatography using 2:1 petrol:diethyl ether as eluant gave 2-hydroxy-3-(1-methyl-cyclohexyl)naphthalene-1,4-dione (296 mg) as a yellow crystalline compound, m.pt.: 79° C.

後処理

  1. temperatureThe mixture was heated for a further hour
  2. customThe organic phase was separated
  3. washwashed successively with water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution
  4. dry with materialbefore drying over magnesium sulphate
  5. filtrationFiltration and evaporation of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-1d1f8cc128424d1786d6f53d18583f6c
出典データセット
uspto-grants-1999_10
特許番号
US05962002

反応ノート

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