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

HRID 397105

Reaction equation

HRID 397105 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-619431b9741c4897aae74f258ed06159
Source dataset
uspto-grants-2003_08
Patent number
US06608220B1

Linked notes

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