Hydrochloric Acid → (3-bromophenoxy)acetic acid

HRID 1979073Notes

Reaction equation

HRID 1979073 reaction equation
O.[OH-].[Li+].[Br:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[O:8][CH2:9][C:10]([O:12]C)=[O:11].Cl>O.C1COCC1>[Br:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[O:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 13827038Acetic acid, 2-(3-bromophenoxy)-, methyl ester

Product 1

HCID 702285(3-bromophenoxy)acetic acidYield 98.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

At 0° C., lithium hydroxide monohydrate (8.41 g, 0.2 mol) is added to a solution of methyl 3-bromophenoxyacetate (19.66 g, 80 mmol) in solution in 100 ml of a water-THF mixture (3:1). Agitation is continued for 15 minutes at 0° C. and then the mixture is acidified by a 3N aqueous solution of hydrochloric acid. It is extracted with ether, dried over MgSO4, filtered and evaporated. 18.21 g of 3-bromophenoxyacetic acid is obtained (yield=98%).

Workup

  1. extractionIt is extracted with ether
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ac9c8445c1b147b08c0517fc6cfaf766
Source dataset
uspto-grants-2001_05
Patent number
US06239284B1

Reaction notes

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