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3-Methoxyphenol → Dimethyl-(3-methoxyphenoxy)malonate

HRID 8605
Notes
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Reaction equation

HRID 8605 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+].[CH3:16][O:17][C:18](=[O:25])[CH:19](Cl)[C:20]([O:22][CH3:23])=[O:21]>CC(C)=O>[CH3:16][O:17][C:18](=[O:25])[CH:19]([O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:20]([O:22][CH3:23])=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 120070Dimethyl chloromalonate

Product 1

HCID 21803851Dimethyl-(3-methoxyphenoxy)malonate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 3-methoxyphenol (115 g) in acetone (1000 ml) was added K2CO3 (115 g). The suspension was stirred at 40° C. for 15 min. A solution of dimethylchloromalonate (133 ml) in acetone was added over a period of 45 min. The resulting brown suspension was stirred overnight at 70° C. Finally, the solvent was removed under reduced pressure and the residue was taken up in water (1000 ml) and extracted twice with DCM (500 ml). The combined organic layers were washed with water (500 ml), dried over Na2SO4, and evaporated to give crude dimethyl-(3-methoxyphenoxy)malonate (230 g) as an orange oil. The product was not purified any further.

Workup

  1. stirringThe resulting brown suspension was stirred overnight at 70° C
  2. customFinally, the solvent was removed under reduced pressure
  3. extractionextracted twice with DCM (500 ml)
  4. washThe combined organic layers were washed with water (500 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-e984f0b46860489fa5ffafd050372951
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091201B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes