Benzoate → Benzoic Acid

HRID 1064220Notes

Reaction equation

HRID 1064220 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:1]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 242BenzoateHCID 14797Potassium Hydroxide

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

First, 1,3,4,5,6-pentamethyl-Dewar benzene-2-carboxylic acid was synthesized. Ethyl 1,3,4,5,6-pentamethyl Dewar benzoate (5.0 g) was combined with 3.80 g of potassium hydroxide in 50 mL methanol. This solution was stirred at gentle reflux for 16 hours. All methanol was then removed by rotary evaporation, and the resulting residue was dissolved in 75 mL water. To this solution was added 10% HCl (aq) dropwise until the pH of the solution was acidic. The resulting white precipitate was collected by vacuum filtration and dried in a vacuum desiccator overnight to yield 3.70 g of dry white solid (85% yield). The product was analyzed by 1H NMR (CDCl3) δ 2.04 (s, 3H); 1.62 (m, 3H); 1.58 (m, 3H); 1.24 (s, 3H); 1.16 (s, 3H).

Workup

  1. temperatureat gentle reflux for 16 hours
  2. customAll methanol was then removed by rotary evaporation
  3. dissolutionthe resulting residue was dissolved in 75 mL water
  4. additionTo this solution was added 10% HCl (aq) dropwise until the pH of the solution
  5. filtrationThe resulting white precipitate was collected by vacuum filtration
  6. customdried in a vacuum desiccator overnight

Sources & evidence

ORD record
ord-aafee2ba53b34b92a3ae00421e92e32b
Source dataset
uspto-grants-2005_11
Patent number
US06969578B2

Reaction notes

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