Carbon Dioxide → 3-Benzyloxy-2-methyl-benzoic acid

HRID 1416076Notes

Reaction equation

HRID 1416076 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[C:11]([Mg]Cl)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](=[O:20])=[O:19]>>[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:18]([OH:20])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 280Carbon DioxideHCID 178431332HCID 178431332, compound

Product 1

HCID 118068023-Benzyloxy-2-methyl-benzoic acid

Procedure

The reaction of (3-benzyloxy-2-methylphenyl)magnesium chloride with carbon dioxide to give 3-benzyloxy-2-methylbenzoic acid can be carried out such that excess carbon dioxide gas is passed into the solution of the Grignard reagent (5) in THF. The alternative exists of initially introducing THF while passing in carbon dioxide gas and adding the Grignard solution. In this case, a suspension of the magnesium chloride salt of the acid (6) is formed first. The salt is hydrolyzed with sufficient aqueous mineral acid, preferably aqueous hydrochloric acid, such that the free acid (6) is completely liberated.

Sources & evidence

ORD record
ord-6748975a2ec8436ba16f11f4c781c185
Source dataset
uspto-grants-1999_06
Patent number
US05910605

Reaction notes

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