Sodium Thiosulfate → 2-Methoxymethyloxy-4,5,6-trimethoxyphenol

HRID 248557Notes

Reaction equation

HRID 248557 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[C:6]=1C=O.ClC1C=CC=C(C(OO)=[O:27])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[C:6]=1[OH:27]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 200957082-Methoxymethyloxy-4,5,6-trimethoxybenzaldehyde

Product 1

HCID 200957092-Methoxymethyloxy-4,5,6-trimethoxyphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12.8 g of 2-methoxymethyloxy-4,5,6-trimethoxybenzaldehyde prepared in Referential Example 11 was dissolved in 100 ml of dichloromethane, and 8.7 g of m-chloroperbenzoic acid was added thereto at room temperature while stirring. The mixture was refluxed for 30 min and cooled with ice, and 100 ml of a saturated aqueous sodium thiosulfate solution was added thereto. The precipitated crystals were separated by filtration. The mother liquor was washed with a saturated aqueous sodium hydrogen-carbonate solution, dried over anhydrous magnesium sulfate and concentrated. The residue was mixed with 50 ml of ethanol, 40 ml of water and 21.3 g of potassium hydroxide, and the mixture was stirred for 1 hr under reflux. The reaction mixture was cooled, poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off to prepare 11.5 g of the product compound (light yellow oleaginous) as a crude product.

Workup

  1. temperatureThe mixture was refluxed for 30 min
  2. additionwas added
  3. customThe precipitated crystals were separated by filtration
  4. washThe mother liquor was washed with a saturated aqueous sodium hydrogen-carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. additionThe residue was mixed with 50 ml of ethanol, 40 ml of water and 21.3 g of potassium hydroxide
  8. stirringthe mixture was stirred for 1 hr
  9. temperatureunder reflux
  10. temperatureThe reaction mixture was cooled
  11. additionpoured into dilute hydrochloric acid
  12. extractionextracted with ethyl acetate
  13. washThe organic phase was washed with water
  14. dry with materialdried over anhydrous magnesium sulfate
  15. distillationthe solvent was distilled off
  16. customto prepare 11.5 g of the product compound (light yellow oleaginous) as a crude product

Sources & evidence

ORD record
ord-a9d4fd00379c45f0b1a834239e7a8aa7
Source dataset
uspto-grants-1993_05
Patent number
US05210239

Reaction notes

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