Hydrochloric Acid → Diethyl 2-acetyl-2-phenylmalonate

HRID 2212314Notes

Reaction equation

HRID 2212314 reaction equation
[C:1]1([CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-:18][CH2:19][CH3:20].[Na+].C(Cl)(=O)C.Cl>O1CCCC1>[C:19]([C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:18])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 66514Diethyl phenylmalonateHCID 2723922Sodium ethoxide

Product 1

HCID 21964398Diethyl 2-acetyl-2-phenylmalonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diethyl 2-phenylmalonate (100 mmol) in anhydrous tetrahydrofuran (300 mL) is added sodium ethoxide (110 mmol). The mixture is stirred at room temperature for 30 minutes, followed by the addition of a solution of acetyl chloride (110 mmol) in tetrahydrofuran (50 mL). After the addition is complete, the mixture is heated to reflux for 3 hours, cooled to room temperature, neutralized with 2 N HCl, then concentrated in vacuo. The residue is partitioned between H2O and CHCl3, the organic extracts washed with sodium bicarbonate, water, and brine, dried (MgSO4), filtered and concentrated.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 3 hours
  4. temperaturecooled to room temperature
  5. concentrationconcentrated in vacuo
  6. customThe residue is partitioned between H2O and CHCl3
  7. washthe organic extracts washed with sodium bicarbonate, water, and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b4732fc65736406a8af8d2caaf1cff8d
Source dataset
uspto-grants-2006_09
Patent number
US07101905B2

Reaction notes

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