Salicylic Acid → Methyl Salicylate

HRID 2269894Notes

Reaction equation

HRID 2269894 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].S(=O)(=O)(O)O.[CH3:16]O>ClCCl>[C:1]([O:10][CH3:16])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 4133Methyl Salicylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine salicylic acid (19.4 g, 140.5 mmol), sulfuric acid (20 mL), and methanol (100 mL). Heat to reflux. After 18 hours, pour the reaction mixture into dichloromethane. Separate the layers and extract the aqueous layer twice with dichloromethane. Combine the organic layers and extract three times with 5%.aqueous sodium bicarbonate solution. Dry the organic layer over MgSO4, filter and evaporate invacuo to give methyl salicylate: Rf=0.60 (silica gel, 1/10 ethyl acetate/hexane).

Workup

  1. temperatureHeat to reflux
  2. customSeparate the layers
  3. extractionextract the aqueous layer twice with dichloromethane
  4. extractionextract three times with 5%
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate invacuo

Sources & evidence

ORD record
ord-5eb9572f37e243a6b4a5613da7bddbd0
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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