Sodium Thiosulfate → 1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine

HRID 397105

반응식

HRID 397105 반응식
[CH3:1][C:2]1([CH3:12])[N:7]([O])[C:6]([CH3:10])([CH3:9])[CH2:5][CH:4]([OH:11])[CH2:3]1.[Br-].[K+].C(=O)(O)[O-:16].[Na+].Cl[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O.ClCCl>[CH3:1][C:2]1([CH3:12])[N:7]([OH:16])[C:6]([CH3:10])([CH3:9])[CH2:5][CH:4]([OH:11])[CH2:3]1

참가 물질

8

반응물 5

HCID 24477Sodium ThiosulfateHCID 137994TempolHCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 23665760Sodium Hypochlorite

생성물 1

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidine

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A mixture of bisnoralcohol (I, 4 g), 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (4-hydroxy-TEMPO, 10 mg), potassium bromide (133 mg), sodium bicarbonate (133 mg), dichloromethane (14 ml) and water (2.2 ml) are cooled to 1°. While maintaining this temperature, aqueous sodium hypochlorite (14%, 6.3 ml) is added over a five hr period. The reaction is complete and aqueous sodium thiosulfate is added, the two phases were separated, and the bisnoraldehyde product is crystallized by replacing the dichloromethane with heptane to give the title compound, mp=153-154°; NMR (CDCl3) 9.56, 5.73, 2.2-2.5, 1.2-2.1, 1.20, 1.10, 0.79 δ; [α]D22=+83.4° (methylene chloride, c=1).

후처리

  1. temperatureare cooled to 1°
  2. additionis added over a five hr period
  3. customthe two phases were separated
  4. customthe bisnoraldehyde product is crystallized

출처 및 근거

ORD 기록
ord-619431b9741c4897aae74f258ed06159
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608220B1

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