Salicylic Acid → HCID 59253959, compound

HRID 2169753Notes

Reaction equation

HRID 2169753 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4]Cl.[C:7]([OH:16])(=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].C(N([CH2:22][CH3:23])CC)C.[C:24](=O)([O-])[O-:25].[K+].[K+].[I-].[Na+].P(O)([O-])([O-])=[O:33].[Na+].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]([CH2:4][O:15][C:7](=[O:16])[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[O:10][CH2:23][C:22]([O:25][CH3:24])=[O:33])=[O:6]

Participants

8

Reactant 6

HCID 338Salicylic AcidHCID 5238Sodium IodideHCID 7295Methyl chloroacetate2×HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 24203Sodium Phosphate, Dibasic

Product 1

HCID 59253959HCID 59253959, compoundYield 300.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Methylchloroacetate (9.4 g, 86.66 mmol) was added dropwise to a mixture of salicylic acid (10 g, 72.46 mmol) and triethylamine (8.8 g, 86.96 mmol) in acetone (50 ml) and heated to reflux for 10 hrs. Solids were filtered off and potassium carbonate (25 g, 180.89 mmol) was added to the acetone layer together with sodium iodide (2 gm, 13.34 mmol), disodium phosphate (2 g, 14.16 mmol) and methylchloroacetate (9.4 g, 86.66 mmol) and refluxed for 16 hrs. Acetone was distilled off and water (125 ml) added. Crude 93 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×50 ml), with water (2×50 ml), dried over sodium sulphate and distilled. Crude 93 was purified by column chromatography on silica gel using benzene to get pure 93 (12 g, 58.7%) as a syrup.

Workup

  1. temperatureheated
  2. temperatureto reflux for 10 hrs
  3. filtrationSolids were filtered off
  4. temperaturerefluxed for 16 hrs
  5. distillationAcetone was distilled off
  6. additionwater (125 ml) added
  7. extractionCrude 93 was extracted into chloroform
  8. washwashed with 5% sodium bicarbonate solution (2×50 ml), with water (2×50 ml)
  9. dry with materialdried over sodium sulphate
  10. distillationdistilled
  11. customCrude 93 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8ff3776984f94f8e8b61d955bd4ed8e2
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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