Hydrochloric Acid → 4-Bromo-2-isopropylbenzoic acid

HRID 30738Notes

Reaction equation

HRID 30738 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 (0.67 g) in water (1 mL)/1,4-dioxane (3 mL) was stirred at room temperature for 5 days. 2 mol/L hydrochloric acid (10 mL) was added to the mixture, 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-9fff2737c5dc4664b818f92fbba2d2d4
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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