Lithium Hydroxide → 4-Bromo-3-(butyloxy)benzoic acid

HRID 1662335Notes

Reaction equation

HRID 1662335 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8]CCCC)=[O:7])=[CH:4][C:3]=1[O:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[Li+]>C1COCC1.CO>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57467609Butyl 4-bromo-3-(butyloxy)benzoate

Product 1

HCID 577062304-Bromo-3-(butyloxy)benzoic acidYield 92.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 5.1 (0.90 g, 2.7 mmol) in THF/MeOH (2/1) (18 mL), was added lithium hydroxide (6.0 mL, 6.0 mmol). The resulting mixture was stirred overnight at 23° C. and then quenched with excess 1N HCl. The mixture was then extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The crude residue was purified by combiflash (0 to 40% EtOAc/hexanes) to afford a 20.1 (0.68 g, 91% yield).

Workup

  1. customquenched with excess 1N HCl
  2. extractionThe mixture was then extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by combiflash (0 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-62afdeecd4c1410f8709478fd2dffb27
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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