Ethyl bromoacetate → HCID 57772112, compound

HRID 1882302Notes

Reaction equation

HRID 1882302 reaction equation
[C:1]([O:14][CH3:15])(=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:22][CH2:23][O:24][C:25]([CH2:27]Br)=[O:26]>CC(C)=O>[CH3:15][O:14][C:1](=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([O:8][CH2:27][C:25]([O:24][CH2:23][CH3:22])=[O:26])=[C:4]([O:5][CH3:6])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 70164Methyl Syringate

Product 1

HCID 57772112HCID 57772112, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of methyl syringate (100 grams, 472 mmol), anhydrous K2CO3 (250 grams, 1.809 mol) in anhydrous acetone (1200 mL) was added Ethyl bromo acetate (113 grams, 677 mmol) and refluxed for 48 hours. Acetone was distilled and water (1200 mL) was added. Crude 11 was filtered, dried, and recrystallized from toluene to give pure 11 (105 grams, 75%) as a white powder. The melting point was found to be 90.5-92.5° C. The structure was confirmed by I.R and NMR. IHNMR (CDCl3) δ 1.32 (t, 3H, CH2CH3), 3.88 (s, 3H, Ester), 3.90 (s, 6H, OCH3), 4.25 (q, 2H, CH2CH3), 4.69 (s, 2H, OCH2), 7.24 (s, 2H, Ar).

Workup

  1. temperaturerefluxed for 48 hours
  2. distillationAcetone was distilled
  3. additionwater (1200 mL) was added
  4. filtrationCrude 11 was filtered
  5. customdried
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-f4170ab867374d549c60653c941fe492
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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