Lithium Hydroxide → 2-(4-bromo-2-formylphenoxy)acetic acid

HRID 2261072Notes

Reaction equation

HRID 2261072 reaction equation
C(O[O:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[C:8](CC)[C:7]=1[CH:15]=[O:16])(=O)C.[Li+].[OH-:18].[CH2:19]1[CH2:23][O:22]CC1>O>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:19][C:23]([OH:18])=[O:22])=[C:7]([CH:15]=[O:16])[CH:8]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86592254HCID 86592254, compound

Product 1

HCID 9688792-(4-bromo-2-formylphenoxy)acetic acidYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl-2-formyl-4-bromophenoxy acetate (60 g, 0.209 mol), LiOH (7.5 g, 0.31 mol), THF (250 mL) and water (100 mL) was stirred at RT for 24 h. The reaction mixture was concentrated under reduce pressure and residue acidified with 1.5N HCl to pH=2. The solid precipitate obtained was filtered and dried to give 4-bromo-2-formylphenoxy acetic acid (50 g, 94%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe solid precipitate obtained
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-ea236b3ee71940db8ab0cafeb62959f6
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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