Ethyl Bromide → HCID 15506059, compound

HRID 2108720Notes

Reaction equation

HRID 2108720 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH2:13](Br)[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:13]([O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1)[CH3:14]

Participants

5

Reactant 3

HCID 6332Ethyl Bromide2×HCID 11430Potassium CarbonateHCID 39129Methyl 3-Hydroxyphenylacetate

Product 1

HCID 15506059HCID 15506059, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 3-hydroxyphenylacetate (6.4 g, 38.5 mmol) was dissolved in acetone (50 mL). Ethyl bromide (3.5 mL, 46.9 mmol) was added, followed by potassium carbonate (6.37 g, 46 mmol). The reaction was heated to reflux. After 24 hours, more ethyl bromide (3.55 mL, 46.9 mmol) was added and the reaction refluxed for a further 24 hours. The mixture was cooled, filtered and rotary evaporated. The product was dissolved in ethyl acetate and the solution washed with saturated sodium bicarbonate (2×50 mL) and brine, and dried (MgSO4). Removal of solvent revealed methyl 3-ethoxyphenylacetate as an oil that crystallized upon standing. 1H NMR (500 MHz, CDCl3) δ 7.25 (1H, dd), 6.87 (3H, m), 4.08 (2H, q), 3.73 (3H, s), 3.65 (2H, s), 1.45 (3H, t).

Workup

  1. temperatureThe reaction was heated to reflux
  2. temperaturethe reaction refluxed for a further 24 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. dissolutionThe product was dissolved in ethyl acetate
  6. washthe solution washed with saturated sodium bicarbonate (2×50 mL) and brine
  7. dry with materialdried (MgSO4)
  8. customRemoval of solvent revealed methyl 3-ethoxyphenylacetate as an oil that
  9. customcrystallized

Sources & evidence

ORD record
ord-94b266bd8d4b4d659afcffd5d0ac6f61
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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