Hydrochloric Acid → 2-(2-Acetyl-4-bromophenoxy)acetic acid

HRID 2243527Notes

Reaction equation

HRID 2243527 reaction equation
[C:1]([C:4]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:5]=1[O:6][CH2:7][C:8]([O:10]CC)=[O:9])(=[O:3])[CH3:2].[OH-].[Na+].Cl.C(OCC)(=O)C>C(O)C.[Cl-].[Na+].O>[C:1]([C:4]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:5]=1[O:6][CH2:7][C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19261366Ethyl 2-(2-acetyl-4-bromophenoxy)acetate

Product 1

HCID 192613632-(2-Acetyl-4-bromophenoxy)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The crude ethyl (2-acetyl-4-bromophenoxy)acetate was dissolved in ethanol (5 mL). A 2 mol/L aqueous solution of sodium hydroxide (5 mL) was added to the solution, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was made acidic with the addition of 2 mol/L hydrochloric acid (7 mL), and then ethyl acetate and brine were added. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate and n-hexane to afford the title compound (0.85 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was recrystallized from ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-422e44ee2f354598b8a660f044df0e9e
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

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