Acetone → HCID 59253984, compound

HRID 2405172Notes

Reaction equation

HRID 2405172 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[CH:7]=1)[CH3:5].[C:18]([O-])([O-])=[O:19].[K+].[K+].[I-].[Na+].C[C:27]([CH3:29])=[O:28]>>[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:29][C:27]([O:19][CH3:18])=[O:28])[CH:12]=2)[CH:7]=1)[CH3:5]

Participants

5

Reactant 4

HCID 180AcetoneHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 5988972-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester

Product 1

HCID 59253984HCID 59253984, compoundYield 54.3%

Procedure

To a mixture of 2-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester 30 (175 grams, 761 mmol), anhydrous K2CO3 (315 grams, 2.279 mmol), sodium iodide (21 grams, 140 mmol) in anhydrous acetone (2000 mL) was added methyl Chloro acetate (104 grams, 958 mmol) and refluxed for 6 hours. Acetone was distilled and water (1500 mL) was added. Crude 31 was extracted into Ethyl acetate, dried over Na2SO4, distilled and purified by column chromatography on silica gel using Benzene as eluant to give pure 31 (125 grams, 54.3%) as a pale yellow syrup. The structure was confirmed with NMR. IHNMR (CDCl3) δ 1.57 (d,3H,CH3), 3.64 (s,3H,Ester), 3.78 (s,3H,Ester), 3.80(q,1H,CH), 4.70(s,1H,Ar), 7.22(d,1H,Ar), 7.36(m,2H,Ar), 7.68(m,3H,Ar).

Workup

  1. temperaturerefluxed for 6 hours
  2. distillationAcetone was distilled
  3. additionwater (1500 mL) was added
  4. extractionCrude 31 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-44f8f02e333149f082578cd8c5cd29f1
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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