Hydrochloric Acid → 6-Hydroxy-1,3-dioxaindane-5-carbaldehyde

HRID 861877Notes

Reaction equation

HRID 861877 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:3]=2[O:2]1.[CH:11]([O-])([O-])[O:12]CC.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[OH:10][C:7]1[CH:6]=[C:4]2[O:5][CH2:1][O:2][C:3]2=[CH:9][C:8]=1[CH:11]=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68289SesamolHCID 6451240Aluminum(III) ChlorideHCID 53630039Ethylorthoformate

Product 1

HCID 67106266-Hydroxy-1,3-dioxaindane-5-carbaldehydeYield 35%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of sesamol (8.28 g), ethyl orthoformate (53.58 g) and benzene (120 ml), powdered anhydrous aluminum chloride (12.0 g) was added, followed by stirring at room temperature for 1 hour. The mixture was then poured into 5% hydrochloric acid (180 ml) and stirred at room temperature for 30 minutes. After the insoluble substance was filtered off, the filtrate was extracted with ether. The ether layer was washed with water and dried (MgSO4), after which the solvent was evaporated off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:8, v/v) to yield 2-hydroxy-4,5-methylenedioxybenzaldehyde (3.48 g, 35%) having a melting point of 128°-129° C.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 30 minutes
  3. filtrationAfter the insoluble substance was filtered off
  4. extractionthe filtrate was extracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialdried (MgSO4)
  7. customafter which the solvent was evaporated off
  8. washeluted with ethyl acetate-hexane (1:8, v/v)

Sources & evidence

ORD record
ord-7130543f4f23462daed28ef47c72885b
Source dataset
uspto-grants-1998_02
Patent number
US05716944

Reaction notes

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