Hydrochloric Acid → HCID 11264354, compound

HRID 2304848Notes

Reaction equation

HRID 2304848 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:10][CH:9]([OH:11])[CH2:8][C@@H:7]([O:12][C:13](=[O:15])[CH3:14])[CH2:6]1)(=[O:3])[CH3:2].[K+].[Br-].C([O-])(O)=O.[Na+].[O-]Cl.[Na+].Cl>ClCCl.O>[C:1]([O:4][C@@H:5]1[CH2:10][C:9](=[O:11])[CH2:8][C@@H:7]([O:12][C:13](=[O:15])[CH3:14])[CH2:6]1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 11183526HCID 11183526, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 11264354HCID 11264354, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 30.00 g of (1R,3R)-1,3-diacetoxy-5-hydroxy-cyclohexane in 400 ml of dichloromethane was subsequently added at 0° a solution of 1.155 g of KBr in 200 ml of water and 325 mg of 2,2,6,6-tetramethyl-piperidine-1-oxyl, radical and the pH was adjusted to 7.0 by addition of 1 ml of aqueous sat. NaHCO3. The stirred mixture was treated simultaneously within 40 min with 107 g of NaOCl (10.6%) and 520 ml of aqueous 0.1 N hydrochloric acid keeping the pH at 7-8. The layers were separated, the organic layer was washed with 15% aqueous NaCl, dried over MgSO4 and evaporated to give 28.93 g of the pure (t.l.c.) title compound as a yellow oil. IR (nujol): 1728s, br. (C═O).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with 15% aqueous NaCl
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-700cdfa0769c484bb358a44116ac97fb
Source dataset
uspto-grants-2002_08
Patent number
US06437142B1

Reaction notes

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