Malonic Acid → diphenyl malonate

HRID 639690Notes

Reaction equation

HRID 639690 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].[C:8]1(O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.P(Cl)(Cl)(Cl)=O>O>[C:1]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])[CH2:2][C:3]([O:5][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 996PhenolHCID 24813Phosphorus oxychloride

Product 1

HCID 2783479diphenyl malonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Malonic acid (11 g, 106 mmol) was mixed with phenol (20 g, 212 mmol) at 0° C. under nitrogen and phosphorus oxychloride (11.5 mL, 123 mmol) was added dropwise to the solid mixture. The resulting mixture was stirred at 0° C. for 5 mins, and then heated at reflux for 5 h, causing the solid to melt and an orange solution to form. The reaction was cooled to room temperature, and then poured onto 100 mL water and extracted with diethyl ether (3×75 mL). The combined organics were washed with brine, dried over MgSO4, concentrated in vacuo to an orange oil of the title compound. (27 g, 99%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 h
  3. customan orange solution to form
  4. temperatureThe reaction was cooled to room temperature
  5. extractionextracted with diethyl ether (3×75 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo to an orange oil of the title compound

Sources & evidence

ORD record
ord-be0d60113c824849893287499715a2ac
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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