Methanol → 5-Bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-benzoic acid

HRID 730173Notes

Reaction equation

HRID 730173 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=1[CH3:21].[OH-].[K+].O.CO>C1COCC1>[Br:10][C:8]1[CH:7]=[CH:6][C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=2[CH3:21])=[C:4]([CH:9]=1)[C:3]([OH:22])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 578344795-Bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-benzoic acid methyl ester

Product 1

HCID 578344875-Bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-benzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude 5-bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-benzoic acid methyl ester 6 was stirred with 50% KOH solution (5 mL), water (30 mL), methanol (12 mL), and THF (30 mL), heated at reflux temperature for three hours and concentrated in vacuo to remove the organic solvents. The resultant aqueous suspension was acidified using 1.0 N HCl solution and filtered. The filtercake was dried over night to give the benzoic acid 7 as a white solid, 4.74 g; 98% yield.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for three hours
  3. concentrationconcentrated in vacuo
  4. customto remove the organic solvents
  5. filtrationfiltered
  6. customThe filtercake was dried over night

Sources & evidence

ORD record
ord-8a1ed2b545ce47fda7b52d8157ad4703
Source dataset
uspto-grants-2009_09
Patent number
US07582667B2

Reaction notes

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