Acetone → HCID 68979033, compound

HRID 1882303Notes

Reaction equation

HRID 1882303 reaction equation
[C:1]([O:14][CH3:15])(=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1.[C:16]([O-])([O-])=[O:17].[K+].[K+].[I-].[Na+].P(O)([O-])([O-])=O.[Na+].[Na+].C[C:32]([CH3:34])=[O:33]>>[CH3:15][O:14][C:1](=[O:13])[CH:2]=[CH:3][C:4]1[CH:12]=[CH:11][C:9]([O:10][CH2:34][C:32]([O:17][CH3:16])=[O:33])=[C:6]([O:7][CH3:8])[CH:5]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 24203Sodium Phosphate, DibasicHCID 5357283Methyl Ferulate

Product 1

HCID 68979033HCID 68979033, compoundYield 70.6%

Procedure

To a mixture of methyl ferulate (38 grams, 183 mmol), anhydrous K2CO3 (88 grams, 637 mmol), Sodium iodide (8 grams, 53 mmol), disodium phosphate (8 grams, 56 mmol) in anhydrous acetone (800 mL) was added methyl chloro acetate (27.2 grams, 251 mmol) and refluxed for 10 hours. Acetone was distilled and water (750 mL) was added. Crude 20 was filtered and recrystallized from methanol and further purified by column chromatography on silica gel using chloroform as eluant to give pure 20 (36 grams, 70.6%) as a white powder. The melting point found to be 105-106.8° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3) δ 3.80 (s, 6H, ester), 3.92 (s, 3H, —OCH3), 4.64 (s, 2H, OCH2), 6.26 (d, 1H, J=17.5 Hz, CH═CH), 6.78 (d, 1H, Ar), 7.05 (m, 2H, Ar), 7.60 (d, 1H, J=17.5 Hz, CH═CH).

Workup

  1. temperaturerefluxed for 10 hours
  2. distillationAcetone was distilled
  3. additionwater (750 mL) was added
  4. filtrationCrude 20 was filtered
  5. customrecrystallized from methanol
  6. customfurther purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5b3b8b24e40043a7a373abcc319c72f9
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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