Hydrochloric Acid → 4-Bromo-2-isopropylbenzoic acid

HRID 2220607Notes

Reaction equation

HRID 2220607 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.O.[OH-].[Li+].O1CCOCC1.Cl>O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 22171591Methyl 4-bromo-2-isopropylbenzoate

Product 1

HCID 230907834-Bromo-2-isopropylbenzoic acidYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-bromo-2-isopropylbenzoate (0.41 g) and lithium hydroxide monohydrate (0.669 g) in water (1 mL)/1,4-dioxane (3 mL) was stirred at room temperature for 5 days. To the reaction mixture was added 2 mol/L hydrochloric acid (10 mL), and the resulting mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate/n-hexane to afford the title compound (0.276 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-40fd82518c3040678d2e2dc43c2ef6fb
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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