1-Methylcyclohexanecarboxylic acid → HCID 178421666, 화합물

HRID 1737147노트

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HRID 1737147 반응식
[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

참가 물질

8

반응물 3

HCID 707441-Methylcyclohexanecarboxylic acidHCID 9855511Ammonium peroxysulphateHCID 178516607HCID 178516607, 화합물

생성물 1

HCID 178421666HCID 178421666, 화합물수율 19.2%

시약·촉매·용매 4

HCID 24470Silver Nitrate촉매HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

반응 조건

온도
20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1d1f8cc128424d1786d6f53d18583f6c
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962002

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