Hydroquinone → (-)-p-(2-Cyano-2-methylhexyloxy)phenol

HRID 1461200ノート

反応式

HRID 1461200 の反応式
C1(C)C=CC(S(O[CH2:11][C:12]([C:18]#[N:19])([CH3:17])[CH2:13][CH2:14][CH2:15][CH3:16])(=O)=O)=CC=1.[C:21]1([CH:28]=[CH:27][C:25]([OH:26])=[CH:24][CH:23]=1)[OH:22].[O-]CCCC.[Na+].[OH-].[Na+].[Cl-].[Na+]>C(O)CCC>[C:18]([C:12]([CH3:17])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11][O:22][C:21]1[CH:28]=[CH:27][C:25]([OH:26])=[CH:24][CH:23]=1)#[N:19]

参加物

7

反応物 5

HCID 785HydroquinoneHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 147934682-Cyano-2-methylhexyl p-toluenesulfonateHCID 23669364Sodium n-butylate

生成物 1

HCID 14793469(-)-p-(2-Cyano-2-methylhexyloxy)phenol収率 21.4%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒2 回

反応条件

温度
120 °C

実験手順

While 480 mg (1.6 mM) of (+) 2-cyano-2-methylhexyl p-toluenesulfonate, 357 mg (3.2 mM) of hydroquinone and 1.5 ml of n-butanol were stirred in a nitrogen atmosphere, sodium butoxide obtained by dissolving 83.3 mM (2.1 mM) of sodium hydroxide in 2.2 ml of n-butanol was added dropwise, followed by stirring for 20 hours under heating at 120° C. After the reaction, 5 ml of saturated sodium chloride aqueous solution was added, followed by extraction with ether. The ether layer was washed with distilled water and dried on sodium sulfate, followed by distilling-off of the solvent to obtain 296 mg of a crude product, which was then purified by thine layer chromatography (developer solvent: methylene chloride) to obtain 81.3 mg of (-)-p-(2-cyano-2-methylhexyloxy)phenol (Yield: 19.1%). [α]D -1.8 degree (c 0.836, benzene).

後処理

  1. customobtained
  2. additionwas added dropwise
  3. additionwas added
  4. extractionfollowed by extraction with ether
  5. washThe ether layer was washed with distilled water
  6. customdried on sodium sulfate
  7. customto obtain 296 mg of a crude product, which
  8. customwas then purified by thine layer chromatography (developer solvent: methylene chloride)

出典と根拠

ORDレコード
ord-af58d263978c43d4bd8e72a5f4f5c970
出典データセット
uspto-grants-1991_12
特許番号
US05075031

反応ノート

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