Sodium Thiosulfate → HCID 13204035, compound

HRID 1199852Notes

Reaction equation

HRID 1199852 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:23][CH3:24])(=[O:22])[CH2:13][C@H:14]([CH2:16][CH2:17][CH:18]=C(C)C)[CH3:15].S([O-])([O-])(=O)=S.[Na+].[Na+].O.O.I(O)(=O)(=O)=O>ClCCl.C1COCC1.O>[CH3:15][C@@H:14]([CH2:16][CH2:17][CH:18]=[O:9])[CH2:13][C:12]([O:23][CH3:24])=[O:22]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 11745305Methyl (3S)-3,7-dimethyloct-6-enoateHCID 86590690HCID 86590690, compound

Product 1

HCID 13204035HCID 13204035, compoundYield 100.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7.76 g (36 mmol) of 80% m-chloroperbenzoic acid in 200 ml of dry dichloromethane is added a solution of 6.00 g (32.6 mmol) of (S)-methyl citronellate 30 (prepared in 31-(1)) in 50 ml of dry dichloromethane, and the mixture is stirred at room temperature for one hour. The reaction mixture are added 5% aqueous solution of sodium thiosulfate and a dilute aqueous solution of sodium hydrogencarbonate, and the mixture is extracted with dichloromethane twice. The extract is washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. To a solution of the residue in 80 ml of THF is added a solution of 8.90 g (39 mmol) of periodic acid dihydrate in 80 ml of THF at 0° C. After additional stirring at room temperature for 20 minutes, the reaction mixture is diluted with water, and extracted with ether twice. The extract is washed with water, a saturated aqueous solution of sodium hydrogencarbonate, and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to give 5.2 g of the crude desired aldehyde 31 as an oil, which is employed in the next step without further purification.

Workup

  1. extractiona dilute aqueous solution of sodium hydrogencarbonate, and the mixture is extracted with dichloromethane twice
  2. washThe extract is washed with a saturated aqueous solution of sodium hydrogencarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. stirringAfter additional stirring at room temperature for 20 minutes
  6. extractionextracted with ether twice
  7. washThe extract is washed with water
  8. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-aaae1034c01a420da13133af5a670a35
Source dataset
uspto-grants-1990_02
Patent number
US04902811

Reaction notes

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