Water → 2-(2-Acetyl-4-bromophenoxy)acetic acid

HRID 1403487Notes

Reaction equation

HRID 1403487 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+].O>C1COCC1>[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

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19261366Ethyl 2-(2-acetyl-4-bromophenoxy)acetate

Product 1

HCID 192613632-(2-Acetyl-4-bromophenoxy)acetic acidYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(2-acetyl-4-bromophenoxy)acetate (8.9 g, 29.56 mmol) in THF (60 mL) was added sodium hydroxide (1.43 g, 35.75 mmol) and water (10 mL). The resulting solution was stirred overnight at room temperature and concentrated under vacuum. The residue was dissolved in water (30 mL) and adjusted to pH 2 with HCl (3N). The solids were collected by filtration to afford 2-(2-acetyl-4-bromophenoxy)acetic acid as a light yellow solid (6.3 g, 78%).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-5876a301a10d45ca9fb90752ad97b047
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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