Reaction #640549

Reaction equation

methyl 2-methyl-4-trimethylsilyloxybenzoate

LiOH

HCl

→

2-methyl-4-hydroxybenzoic acid

Yield 31.6%

Solvents

—

ethyl acetate hexanes

methanol

water

Conditions

Workup

1. 1
   OtherA 100 mL round bottom flask equipped with magnetic stir bar
2. 2
   TemperatureAfter 2 hours at reflux the reaction
3. 3
   ExtractionExtraction with ethyl acetate
4. 4
   Concentrationfollowed by concentration in vacuo
5. 5
   Othergave a crude solid (70:30) product

Procedure

A 100 mL round bottom flask equipped with magnetic stir bar was charged with 5.7 g methyl 2-methyl-4-trimethylsilyloxybenzoate and 2.0 g LiOH in 40 mL methanol and 10 mL water. After 2 hours at reflux the reaction was poured into 10 mL concentrated HCl and then 100 g ice. Extraction with ethyl acetate followed by concentration in vacuo gave a crude solid (70:30) product:starting material. Flash Chromatography using 50-50 ethyl acetate/hexanes as an eluent gave 1.15 g 2-methyl-4-hydroxybenzoic acid, m/e=193(M+H).

Source