Salicylic Acid → HCID 10176491, compound

HRID 1586520Notes

Reaction equation

HRID 1586520 reaction equation
[OH-].[K+].[C:3]([OH:12])(=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].[C:13]([O-])(=O)[C:14]1[C:15](=CC=CC=1)[OH:16].[K+].C(Cl)(=O)C=C.FC(F)(F)C(O)=O>CO.C1C=CC=CC=1.O.C(OCC)C>[C:15]([O:6][C:5]1[C:4](=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:12])=[O:11])(=[O:16])[CH:14]=[CH2:13]

Participants

10

Reactant 5

HCID 338Salicylic AcidHCID 6422Trifluoroacetic acidHCID 13140Acryloyl chlorideHCID 14797Potassium HydroxideHCID 23664627Potassium salicylate

Product 1

HCID 10176491HCID 10176491, compound

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Potassium hydroxide (11.2 g, 0.2 mole) was dissolved in 50 ml of methanol and salicylic acid (13.8 g, 0.1 mole) was added. The formed precipitate was separated and dried in vacuum. The precipitate (0.1 mole, 17.6 g) of potassium salicylate was dissolved in 50 ml of benzene, heated to boiling and acryloyl chloride (22.1 g, 0.2 mole) was added with intense stirring for 2 hours. The formed precipitate was centrifuged, the benzene solution was evaporated using a rotor evaporator and the formed solid product, potassium acryloyl salicylate, was dried in a vacuum. The prepared salt (12.8 g, 0.06 mole) was dissolved in 150 ml of distilled water and 150 ml of a 20% solution of trifluoroacetic acid was added. The formed emulsion was stirred for 40 min. Then, 300 ml of diethyl ether was added and the mixture was stirred for 5-6 hours. The ether layer was separated, dried over magnesium sulfate, and evaporated in a vacuum to a dry state. The white precipitate was recrystallized from benzene. The yield of ASA from the mixture was 30%.

Workup

  1. customThe formed precipitate was separated
  2. customdried in vacuum
  3. temperatureheated
  4. customthe benzene solution was evaporated
  5. customa rotor evaporator
  6. dry with materialthe formed solid product, potassium acryloyl salicylate, was dried in a vacuum
  7. stirringThe formed emulsion was stirred for 40 min
  8. stirringthe mixture was stirred for 5-6 hours
  9. customThe ether layer was separated
  10. dry with materialdried over magnesium sulfate
  11. customevaporated in a vacuum to a dry state
  12. customThe white precipitate was recrystallized from benzene

Sources & evidence

ORD record
ord-081d8ea47b104856a7a68bc9eb63f3d4
Source dataset
uspto-grants-1999_08
Patent number
US05945457

Reaction notes

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