O-Cresol → ((4-Hydroxy-3-methylphenyl)sulfanyl)formonitrile

HRID 408672

反応式

HRID 408672 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[S-:9][C:10]#[N:11].[Na+].[Na+].[Br-].BrBr.C([O-])(O)=O.[Na+]>CO>[CH3:1][C:2]1[CH:7]=[C:6]([S:9][C:10]#[N:11])[CH:5]=[CH:4][C:3]=1[OH:8]

参加物

7

反応物 5

HCID 335O-CresolHCID 24408BromineHCID 253881Sodium BromideHCID 516871Sodium thiocyanateHCID 516892Sodium Bicarbonate

生成物 1

HCID 220928((4-Hydroxy-3-methylphenyl)sulfanyl)formonitrile収率 67.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a 250 ml flask were added 10.8 g o-methylphenol, 26.0 g sodium thiocyanate, 70 ml methanol, added dropwise 100 ml methanol solution containing 10.3 g NaBr, 5.3 ml liquid bromine at 0° C. under N2 atmosphere. The mixture was stirred at room temperature for 3 hours. The mixture was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2 for four times. The extract was dried over anhydrous Na2SO4, filtrated, evaporated and purified by column chromatograph (petroleum ether:ethyl acetate=8:1) to obtain 11.1 g yellow solid, yield 67.27%. 1H-NMR (400 MHz, CDCl3, δ ppm) δ 2.2558 (3H, s), 5.0 (1H, s), 6.8 (1H, d, J=8.4 Hz), 7.3605-7.2631 (1H, m), 7.3542 (1H, s).

後処理

  1. extractionextracted with CH2Cl2 for four times
  2. dry with materialThe extract was dried over anhydrous Na2SO4
  3. filtrationfiltrated
  4. customevaporated
  5. custompurified by column chromatograph (petroleum ether:ethyl acetate=8:1)

出典と根拠

ORDレコード
ord-33b17429b9824748931f65f162f6d6d6
出典データセット
uspto-grants-2014_06
特許番号
US08759355B2

関連ノート

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