Acetone → HCID 57772137, compound

HRID 1882301Notes

Reaction equation

HRID 1882301 reaction equation
[C:1]([O:12][CH2:13][CH3:14])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[C:15]([O-])([O-])=[O:16].[K+].[K+].C[C:22]([CH3:24])=[O:23]>>[CH2:13]([O:12][C:1](=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([O:8][CH2:24][C:22]([O:16][CH3:15])=[O:23])=[C:4]([O:5][CH3:6])[CH:3]=1)[CH3:14]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 12038Ethyl vanillate

Product 1

HCID 57772137HCID 57772137, compoundYield 70%

Procedure

To a mixture of Ethyl Vanillate (100 grams, 510 mmol), and anhydrous K2CO3 (300 grams, 2.17 mol) in anhydrous acetone (1000 mL) was added methyl chloro acetate (123.8 grams, 1.14 mmol) and refluxed for 8 hours. Acetone was distilled and water (1500 mL) was added. Crude 8 was filtered, dried, and recrystallized from a mixture of toluene:Hexane (1:5) to give pure 8 (95.7 grams, 70%) as a white powder. The melting point was found to be 72.7-74.3° C. The structure was confirmed by I.R and NMR. IHNMR (CDCl3) δ 1.40 (t, 3H, CH2CH3), 3.80 (s, 3H, Ester), 3.92 (s, 3H, OCH3), 4.38 (q, 2H, OCH2CH3), 4.88 (s, 2H, OCH2), 6.80 (d, 1H, Ar), 7.59 (d, 1H, Ar), 7.66 (dd, 1H, Ar).

Workup

  1. temperaturerefluxed for 8 hours
  2. distillationAcetone was distilled
  3. additionwater (1500 mL) was added
  4. filtrationCrude 8 was filtered
  5. customdried
  6. customrecrystallized from a mixture of toluene:Hexane (1:5)

Sources & evidence

ORD record
ord-ef5aab1a57d94f16b7ef6acd4d9b231e
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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