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

HRID 397105

反応式

HRID 397105 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-619431b9741c4897aae74f258ed06159
出典データセット
uspto-grants-2003_08
特許番号
US06608220B1

関連ノート

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