Hydrochloric Acid → HCID 11830339, compound

HRID 1200131Notes

Reaction equation

HRID 1200131 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].ICI.Cl>O.CS(C)=O>[OH:9][C:8]1[CH:10]=[C:2]([CH:3]=[C:4]2[O:5][CH2:14][O:7][C:6]=12)[C:1]([O:12][CH3:13])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6346DiiodomethaneHCID 7428Methyl GallateHCID 11430Potassium Carbonate

Product 1

HCID 11830339HCID 11830339, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture comprising 34.4 g of commercially available methyl gallate, 25.8 g of anhydrous potassium carbonate, 400 ml of DMSO and 50.0 g of diiodomethane was stirred at 40° C. for 24 hours in a nitrogen current. After the reaction, the liquid mixture was poured into water and made acidic by 2N hydrochloric acid, the mixture was extracted with ethyl acetate, and the extract was washed with water. The solvent was removed from the extract and the residue was subjected to flash column chromatography [466 g of 230-400 mesh silica gel, solvent: n-hexane/acetoine (3/1), pressure: 0.4 kg/cm2, 5th to 9th fractions when fractions of 100 ml were collected] to effect purification and obtain 14.8 g of methyl 3-hydroxy-4,5-(methylenedioxy)benzoate (the yield was 40.4%).

Workup

  1. customAfter the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. customThe solvent was removed from the
  5. extractionextract
  6. customthe residue was subjected to flash column chromatography [466 g of 230-400 mesh silica gel, solvent: n-hexane/acetoine (3/1), pressure: 0.4 kg/cm2, 5th to 9th fractions when fractions of 100 ml were collected]
  7. custompurification

Sources & evidence

ORD record
ord-dc2bda41482e4895b21c62ecd88ac395
Source dataset
uspto-grants-1990_02
Patent number
US04904694

Reaction notes

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