Hydrochloric Acid → Methyl 5-(tert-butyl)-2-methoxybenzoate

HRID 2242349Notes

Reaction equation

HRID 2242349 reaction equation
Cl.[C:2]([C:6]1[CH:7]=[CH:8][C:9]([O:15][CH3:16])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12])([CH3:5])([CH3:4])[CH3:3].[CH3:17]O>>[CH3:17][O:12][C:11](=[O:13])[C:10]1[CH:14]=[C:6]([C:2]([CH3:5])([CH3:3])[CH3:4])[CH:7]=[CH:8][C:9]=1[O:15][CH3:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 70103155-Tert-Butyl-2-Methoxybenzoic Acid

Product 1

HCID 15724682Methyl 5-(tert-butyl)-2-methoxybenzoateYield 95%

Procedure

Hydrogen chloride gas was bubbled for 5 min into a stirred solution of 5-tert-butyl-2-methoxybenzoic acid (5.00 g, 24.0 mmol) in methanol (100 ml) at 0° C., after which time the solution was heated under reflux for 17.5 h. The reaction was cooled, evaporated to dryness under reduced pressure and purified by chromatography on silica using diethyl ether as eluent to afford 5-tert-butyl-2-methoxybenzoic acid methyl ester as a pale cream solid (5.06 g, 95%).

Workup

  1. temperatureafter which time the solution was heated
  2. temperatureunder reflux for 17.5 h
  3. temperatureThe reaction was cooled
  4. customevaporated to dryness under reduced pressure
  5. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-71d8ceecbad14df5be86f1c5ba47b85f
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

Loading…