Acetone → HCID 57772128, compound

HRID 2405169Notes

Reaction equation

HRID 2405169 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C:14]([O-])([O-])=[O:15].[K+].[K+].C[C:21]([CH3:23])=[O:22]>>[CH3:13][O:12][C:10](=[O:11])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:23][C:21]([O:15][CH3:14])=[O:22])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Product 1

HCID 57772128HCID 57772128, compoundYield 36%

Procedure

To a mixture of methyl 3(4-hydroxy phenyl)propionate (60 grams, 333 mmol), anhydrous K2CO3 (180 grams, 1.30 mol) in anhydrous acetone (1 liter) was added methyl chloro acetate (74.2 grams, 684 mmol) and refluxed for 40 hours. Acetone was distilled and water (1000 mL) was added. Crude 15 extracted into chloroform, distilled chloroform and high vacuum distilled to get pure 15 (30 grams, 36%) as a colorless low melting solid. Bp12 210-213° C. The structure was confirmed by NMR. IHNMR (CDCl3) δ 2.58 (t, 2H, CH2), 2.90(t, 2H, CH2), 3.62(s, 3H, ester), 3.80(s, 3H, ester), 4.60(s, 3H, OCH2), 6.80(d, 2H, Ar), 7.12(d, 2H, Ar).

Workup

  1. temperaturerefluxed for 40 hours
  2. distillationAcetone was distilled
  3. additionwater (1000 mL) was added
  4. extractionCrude 15 extracted into chloroform
  5. distillationdistilled chloroform and high vacuum
  6. distillationdistilled

Sources & evidence

ORD record
ord-9d1f51b1d66644ed93d11ff00a666e4e
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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