Water → 2-(2-Acetyl-5-bromophenoxy)acetic acid

HRID 2170485Notes

Reaction equation

HRID 2170485 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:5]=1[O:6][CH2:7][C:8]([O:10]C)=[O:9])(=[O:3])[CH3:2].O.[OH-].[Na+]>O1CCCC1>[C:1]([C:4]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][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 57419482Methyl 2-(2-acetyl-5-bromophenoxy)acetate

Product 1

HCID 2937532-(2-Acetyl-5-bromophenoxy)acetic acidYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(2-acetyl-5-bromophenoxy)acetate (1.35 g, 4.5 mmol) in tetrahydrofuran:water=3:1 (20 mL) was added sodium hydroxide (400 mg, 10 mmol). The mixture was stirred at room temperature for 2 hours. The suspension was concentrated in vacuum and quenched with aqueous 1N hydrochloric acid (5 mL). The residue was taken up with water (50 mL) and extracted with dichloromethane (50 mL). The combined extract was dried over sodium sulphate, evaporated and purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give the product 2-(2-acetyl-5-bromophenoxy)acetic acid (1.14 g, 91%) as pale solid.

Workup

  1. concentrationThe suspension was concentrated in vacuum
  2. customquenched with aqueous 1N hydrochloric acid (5 mL)
  3. extractionextracted with dichloromethane (50 mL)
  4. extractionThe combined extract
  5. dry with materialwas dried over sodium sulphate
  6. customevaporated
  7. custompurified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-05f71feb0fb54e1c8c724635c487bc50
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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