4-Hydroxy-3,5-bis(t-butyl)benzaldoxime → Benzonitrile, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-

HRID 843999

반응식

HRID 843999 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[CH:8]=[N:9]O)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C.C(OCC)C>[C:15]([C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]=1[OH:14])[C:8]#[N:9])([CH3:18])([CH3:17])[CH3:16]

참가 물질

5

반응물 2

HCID 3285904-Hydroxy-3,5-bis(t-butyl)benzaldoximeHCID 516892Sodium Bicarbonate

생성물 1

HCID 137274Benzonitrile, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-수율 54%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 7918Acetic Anhydride용매

반응 조건

온도
0 °C

실험 절차

A solution of 3,5-Di-tert-butyl-4-hydroxy-benzaldehyde oxime (3.0 grams, 8.4 mmole) in acetic anhydride (6 ml) was was refluxed for 2 hours. The mixture was cooled to 0° C. and saturated sodium hydrogencarbonate was added. The mixture was extracted with methylene chloride. The combined extracts were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated to give a solid. This was dissolved in diethyl ether and extracted with 1 N sodium hydroxide which was then acidified to pH 1 and extracted with ethyl acetate. The extract was dried and concentrated to a yellow solid which was recrystalized from ethyl acetate/hexane to give white crystals (1.05 g). MW 231; MS (m/e) 249 (M++NH4+).

후처리

  1. extractionThe mixture was extracted with methylene chloride
  2. washThe combined extracts were washed with saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a solid
  7. extractionextracted with 1 N sodium hydroxide which
  8. extractionextracted with ethyl acetate
  9. customThe extract was dried
  10. concentrationconcentrated to a yellow solid which
  11. customwas recrystalized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-5c09e90a1c474adaa12a8a64284234f3
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380218B1

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