Hydrochloric Acid → Diethyl 2-acetyl-2-phenylmalonate

HRID 270222

Reaction equation

HRID 270222 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 min, 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 H20 and CHCl3, the organic extracts washed with sodium bicarbonate, water, and brine, dried (MgS04), 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 H20 and CHCl3
  7. washthe organic extracts washed with sodium bicarbonate, water, and brine
  8. customdried (MgS04)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d547d0bd329247e984fcbcf80508e4fb
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Linked notes

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