Carbon Dioxide → 2,4,6-Trimethylbenzoic acid

HRID 630554Notes

Reaction equation

HRID 630554 reaction equation
[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[Mg]Br.[C:12](=[O:14])=[O:13]>C(OCC)C>[CH3:11][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 280Carbon Dioxide2×HCID 178425415HCID 178425415, compound

Product 1

HCID 101942,4,6-Trimethylbenzoic acidYield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

20 mL of 2-mesitylmagnesium bromide (1.0 M in diethyl ether, 20 mmol) was added to a flask containing 60 mL of dry diethyl ether and solid carbon dioxide (dry ice). Additional dry ice was added throughout the course of the reaction as needed. After 30 min, the mixture was allowed to warm to room temperature and the solid was separated by filtration. The solid was dissolved in a 1 M KOH(aq) solution followed by neutralization to pH 1 using HCl. This resulted in the precipitation of a white powder that was collected by filtration and dried under vacuum at 80° C. (2.52 g, 77% yield).

Workup

  1. customthe solid was separated by filtration
  2. dissolutionThe solid was dissolved in a 1 M KOH(aq) solution
  3. customThis resulted in the precipitation of a white powder that
  4. filtrationwas collected by filtration
  5. customdried under vacuum at 80° C. (2.52 g, 77% yield)

Sources & evidence

ORD record
ord-4cd05343f62a4806a3e22e2dc52df861
Source dataset
uspto-grants-2016_04
Patent number
US09315630B2

Reaction notes

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