HCID 59316794, compound → 3-Bromo-4-propan-2-yloxybenzoic acid

HRID 1773951Notes

Reaction equation

HRID 1773951 reaction equation
C([O:4][C:5](=[O:17])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([CH3:15])[CH3:14])=[C:8]([Br:16])[CH:7]=1)(C)C>CCO.[OH-].[Na+]>[Br:16][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:5]([OH:17])=[O:4]

Participants

4

Reactant 1

HCID 59316794HCID 59316794, compound

Product 1

HCID 166412393-Bromo-4-propan-2-yloxybenzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-bromo-4-isopropoxy-benzoic acid isopropyl ester (5.32 g, 17.7 mmol, 1 eq.) in EtOH (100 mL), 1M aq. NaOH soln. (80 mL) was added. The resulting solution was heated at 80° C. for 18 hours, then concentrated in vacuo. The resulting aq. layer was carefully acidified with 2N aq. HCl soln. The mixture was extracted with DCM (3×100 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo to give 3-bromo-4-isopropoxy-benzoic acid. The product was used without further purification.

Workup

  1. addition(80 mL) was added
  2. concentrationconcentrated in vacuo
  3. extractionThe mixture was extracted with DCM (3×100 mL)
  4. dry with materialphases were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6655513e4ca34fc197f59742805d37a2
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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