Phenol → 1,3-Diethyl 2-phenoxypropanedioate

HRID 1598533Notes

Reaction equation

HRID 1598533 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CC(C)=O>[O:13]([CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 84182Diethyl chloromalonate

Product 1

HCID 23051671,3-Diethyl 2-phenoxypropanedioateYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

22.1 g (160 mmol) of potassium carbonate were suspended in 30 ml of acetone, 7.5 g (80 mmol) of phenol in 100 ml of acetone were added, and the mixture was refluxed for 1 hour. 15.5 g (80 mmol) of diethyl 2-chloromalonate in 100 ml of acetone were subsequently added dropwise, the mixture was refluxed for 10 hours and evaporated in vacuo, and the residue was taken up in methylene chloride. The organic phase was washed with saturated NaHCO3 solution and saturated NaCl solution, dried over magnesium sulfate and evaporated. Column chromatography (silica gel, heptane/diethyl ether 2:1) of the residue gave 15.5 g (77% of theory) diethyl 2-phenoxymalonate as a colorless liquid.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperaturethe mixture was refluxed for 10 hours
  3. customevaporated in vacuo
  4. washThe organic phase was washed with saturated NaHCO3 solution and saturated NaCl solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-baf4b78b6f154ac89f0bd45c0c87affc
Source dataset
uspto-grants-1998_04
Patent number
US05739079

Reaction notes

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