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

HRID 1461200노트

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HRID 1461200 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

HCID 14793469(-)-p-(2-Cyano-2-methylhexyloxy)phenol수율 21.4%

시약·촉매·용매 1

HCID 2631-Butanol용매2회

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온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-af58d263978c43d4bd8e72a5f4f5c970
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05075031

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