Hydrochloric Acid → 4-Hydroxy-o-toluic acid

HRID 491389

Reaction equation

HRID 491389 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([O:11][Si](C)(C)C)[CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[Li+].[OH-].Cl>CO.O>[CH3:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86609507HCID 86609507, compound

Product 1

HCID 684754-Hydroxy-o-toluic acid

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. additionwas charged with 5.7 g methyl
  3. temperatureAfter 2 hours at reflux the reaction
  4. extractionExtraction with ethyl acetate
  5. concentrationfollowed by concentration in vacuo
  6. customgave a crude solid (70:30) product

Sources & evidence

ORD record
ord-a77939f1109342f1baf61dd0e0d0cebe
Source dataset
uspto-grants-2009_05
Patent number
US07531538B2

Linked notes

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