Hydrochloric Acid → HCID 58629735, compound

HRID 423253Notes

Reaction equation

HRID 423253 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:13][CH3:14])[C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].P([O-])(O)(O)=[O:16].[Na+].S(N)(=O)(=O)O.Cl([O-])=O.[Na+].Cl>O1CCOCC1.O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:13][CH3:14])[C:11]=1[OH:12])[C:7]([OH:16])=[O:8])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 58629750HCID 58629750, compound

Product 1

HCID 58629735HCID 58629735, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-ethoxy-4-hydroxy-5-methoxybenzaldehyde (578 mg), sodium dihydrogenphosphate (1.41 g), and amidosulfuric acid (429 mg) in dioxane (6 mL)-water (10 mL) was added an aqueous solution (3 mL) of sodium chlorite (400 mg) under ice-cooling. The mixture was stirred for 2 hours under ice-cooling. Hydrochloric acid was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was washed with 10% aqueous sodium thiosulfate and saturated brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound (586 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with 10% aqueous sodium thiosulfate and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d01f70975b634c138109276c98a56bae
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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