Sodium Iodide → HCID 59253972, compound

HRID 638701Notes

Reaction equation

HRID 638701 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:12]=2)[CH:7]=1)[CH3:5].[C:23]([O-])([O-])=O.[K+].[K+].[I-].[Na+].ClC(C)C(OC)=O>CC(C)=O>[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH:17]([C:18]([O:20][CH3:21])=[O:19])[CH3:23])[CH:12]=2)[CH:7]=1)[CH3:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 28659Methyl 2-chloropropionateHCID 59253984HCID 59253984, compound

Product 1

HCID 59253972HCID 59253972, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester 7 (150 g, 652 mmol), anhydrous K2CO3 (455 gr, 3.292 mol) and sodium iodide (22.5 grams, 150 mmol) in anhydrous acetone (2000 ml) was added methyl 2-chloropropionate (107.5 g, 877 mmol) and refluxed for 50 hours. Acetone was distilled off and water (1500 ml) was added. Crude 8 was extracted into ethyl acetate, dried over Na2SO4, distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 8 (175 g, 85%) as a light yellow syrup. The structure was confirmed with NMR.

Workup

  1. temperaturerefluxed for 50 hours
  2. distillationAcetone was distilled off
  3. additionwater (1500 ml) was added
  4. extractionCrude 8 was extracted into ethyl acetate
  5. dry with materialdried over Na2SO4
  6. distillationdistilled
  7. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b8e489eeccca4a0e9f3a6b15be94ae06
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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