Hydrochloric Acid → 4-Hydroxy-o-toluic acid

HRID 479741

Reaction equation

HRID 479741 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([O:12][Si](C)(C)C)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[OH-].Cl>CO.O>[CH3:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21879730Methyl 2-methyl-4-trimethylsilyloxybenzoate

Product 1

HCID 684754-Hydroxy-o-toluic acidYield 31.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

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).

Workup

  1. customA 100 mL round bottom flask equipped with magnetic stir bar
  2. temperatureAfter 2 hours at reflux the reaction
  3. extractionExtraction with ethyl acetate
  4. concentrationfollowed by concentration in vacuo
  5. customgave a crude solid (70:30) product

Sources & evidence

ORD record
ord-5bca532660564a6fa621317c7ac27c90
Source dataset
uspto-grants-2003_11
Patent number
US06646010B2

Linked notes

Loading…