Sulfuric Acid → Salicylic Acid

HRID 511698Notes

Reaction equation

HRID 511698 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>[C:4]([OH:6])(=[O:5])[C:3]1[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:1]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 34692,5-Dihydroxybenzoic acid

Product 1

HCID 338Salicylic Acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Conditions

Temperature
50 °C

Procedure

One hundred g of 2,5-dihydroxy benzoic acid and 1,441 g of 80% sulfuric acid were heated to 50° C. and mixed. Tert-butylalcohol (144 g) was added to the dispersion liquid and stirred at 50° C. for 30 minutes. Thereafter, the operation, where 144 g of tert-butylalcohol was added to the dispersion liquid and stirred for 30 minutes, was performed 3 times. The reaction liquid was cooled to room temperature, and slowly added to 1 kg of ice water. The resultant precipitate was collected by filtration, and washed with water and then hexane. The precipitate was dissolved in 200 mL of methanol and reprecipitated in 3.6 L of water. After being collected by filtration, the resultant was dried at 80° C. to thereby obtain 74.9 g of a salicylic acid intermediate represented by the following formula (7).

Workup

  1. additionmixed
  2. stirringstirred for 30 minutes
  3. customThe reaction liquid
  4. temperaturewas cooled to room temperature
  5. filtrationThe resultant precipitate was collected by filtration
  6. washwashed with water
  7. dissolutionThe precipitate was dissolved in 200 mL of methanol
  8. customreprecipitated in 3.6 L of water
  9. filtrationAfter being collected by filtration
  10. customthe resultant was dried at 80° C.

Sources & evidence

ORD record
ord-618cc791f72940c387ef54cb36361223
Source dataset
uspto-grants-2015_08
Patent number
US09098003B2

Reaction notes

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