Sulfuric Acid → Salicylic Acid
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8](O)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.C(O)(C)(C)C>CO>[C:4]([OH:6])(=[O:5])[C:3]1[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
100 g of 2,5-dihydroxybenzoic acid and 1,441 g of 80% sulfuric acid were heated to 50° C. and mixed. To the liquid dispersion obtained, 144 g of tert-butyl alcohol was added, and the mixture was stirred at 50° C. for 30 minutes. Thereafter, the operation that 144 g of tert-butyl alcohol was added to the liquid dispersion and the mixture was stirred for 30 minutes was carried out three times. The reaction solution obtained was cooled to room temperature, and then dropwise added to 1 kg of ice water, where the precipitate formed was filtered, which was then washed with water and further washed with hexane. The precipitate formed was dissolved in 200 mL of methanol, and the solution obtained was re-precipitated in 3.6 L of water. After filtration, the product was dried at 80° C. to obtain 74.9 g of a salicylic acid intermediate represented by the following formula (3).
Workup
- additionmixed
- customTo the liquid dispersion obtained
- stirringthe mixture was stirred for 30 minutes
- customThe reaction solution obtained
- temperaturewas cooled to room temperature
- customformed
- filtrationwas filtered
- washwhich was then washed with water
- washfurther washed with hexane
- customThe precipitate formed
- customthe solution obtained
- customwas re-precipitated in 3.6 L of water
- filtrationAfter filtration
- customthe product was dried at 80° C.
Sources & evidence
- ORD record
- ord-d701586f4e124eb8bcce207b98749d55
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609312B2
Reaction notes
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