Benzoic Acid → Methyl Benzoate

HRID 726826Notes

Reaction equation

HRID 726826 reaction equation
[CH3:1]O.[C:3]([OH:11])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O>[C:3]([O:11][CH3:1])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 887Methanol

Product 1

HCID 7150Methyl BenzoateYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The acid-catalyzed condensation of alcohols to esters has been known for some time. For example, the acid-catalyzed condensation of an alcohol with a carboxylic acid is known to yield an ester and water. This is generally known as a Fischer esterification reaction. It is a reversible process and the equilibrium lies slightly to the side of the production of the products when the reactants are simple alcohols and carboxylic acids. When the reaction is used for preparative purposes, the position of the equilibrium can be made more favorable by using either the alcohol or the carboxylic acid in excess. For example, methanol (0.6 mol.) plus benzoic acid (0.1 mol.) can be reacted to form methyl benzoate (isolated in 70% yield based on benzoic acid) and water. The reaction requires the addition of heat and sulfuric acid as a catalyst. The use of other acids such as, hydrochloric acid and trifluoro acetic acid are also known.

Workup

  1. customThis is generally known as a Fischer esterification reaction

Sources & evidence

ORD record
ord-1fe3fb5a24f84759b0a850a8292c12a8
Source dataset
uspto-grants-1998_01
Patent number
US05710293

Reaction notes

Loading…