4-Isopropylphenol → Diethyl 2-(4-isopropylphenoxy)malonate

HRID 1859962Notes

Reaction equation

HRID 1859962 reaction equation
[H-].[Na+].[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH3:5])[CH3:4].Cl[CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(OCC)(=O)C>CN(C)C=O.C1(C)C=CC=CC=1>[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:8][CH:7]=1)([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 74654-IsopropylphenolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 84182Diethyl chloromalonate

Product 1

HCID 10565722Diethyl 2-(4-isopropylphenoxy)malonateYield 76.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (55% suspension in oil, 5.22 g) was added to a solution of 4-isopropylphenol (15.0 g) in a mixture of dimethylformamide (63 ml) and toluene (75 ml). The mixture was stirred at ambient temperature for 1 hour. To the reaction mixture, diethyl 2-chloromalonate (18.5 g) was added. The mixture was stirred at 60° C. for 2.5 hours. At the end of this time ethyl acetate was added to the reaction mixture. The ethyl acetate layer was separated and washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=4/1 as the eluant to afford the desired compound (21.5 g) as a syrup.

Workup

  1. stirringThe mixture was stirred at 60° C. for 2.5 hours
  2. customThe ethyl acetate layer was separated
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-1270305a3a3240eb9ab07220e67fe02c
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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