Hydrochloric Acid → HCID 90408370, compound

HRID 2275411Notes

Reaction equation

HRID 2275411 reaction equation
[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:13])[C:5]=1[OH:14])[CH:2]=[CH2:3].[OH-].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18].Cl>O>[C:17]([O:14][C:5]1[C:6]([CH3:13])=[C:7]([CH:11]=[CH:12][C:4]=1[CH2:1][CH:2]=[CH2:3])[C:8]([OH:10])=[O:9])(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 90408616HCID 90408616, compound

Product 1

HCID 90408370HCID 90408370, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Allyl-3-hydroxy-2-methylbenzoic acid (2.0 g, 10.4 mmol) was slurried in 6 ml water in a 500 ml round bottom flask, cooled in an ice bath, and stirred. Aqueous NaOH solution (4.2 g of 50% NaOH in 6 ml water) was added slowly. The mixture was stirred for few minutes until the solution was clear. Acetic anhydride was added drop wise until pH 6 was obtained, by that time the reaction mixture become a thick slurry with an off white color. The mixture was stirred overnight at room temperature. The reaction mixture became a thick white slurry. The pH was adjusted to 2 with conc. HCl. A precipitate formed, and was filtered under vacuum and dried. The combined dried product was dissolved in DCM and purified on an ISCO system using 40 g silica column and hexane/EtOAc solvent gradient. The product eluted ˜30% EtOAc in hexane, and the fractions were collected and dried under vacuum to give (2.4 g, 98%) SKC-01-116. 1H NMR (400 MHz, CDCl3) δ 12.0 (br s, 1H), 7.92 (d, J=8.1 Hz, 1H), 7.18 (d, J=8.1 Hz, 1H), 6.03-5.67 (m, 1H), 5.26-4.89 (m, 2H), 3.31 (d, J=6.6 Hz, 2H), 2.44 (s, 3H), 2.37 (s, 3H).

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe mixture was stirred for few minutes until the solution
  3. customwas obtained, by that time the reaction mixture
  4. stirringThe mixture was stirred overnight at room temperature
  5. customA precipitate formed
  6. filtrationwas filtered under vacuum
  7. customdried
  8. dissolutionwas dissolved in DCM
  9. custompurified on an ISCO system
  10. washThe product eluted ˜30% EtOAc in hexane
  11. customthe fractions were collected
  12. customdried under vacuum
  13. customto give (2.4 g, 98%) SKC-01-116

Sources & evidence

ORD record
ord-71abc89477284f99a8c5711ea617a055
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

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