Guaiacol → Dimethyl 2-(2-methoxyphenoxy)malonate

HRID 2085076Notes

Reaction equation

HRID 2085076 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].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:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 120070Dimethyl chloromalonate

Product 1

HCID 12967085Dimethyl 2-(2-methoxyphenoxy)malonate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
45 °C

Procedure

48 ml 2-methoxy-phenol (guajacol) were slowly added to a stirred suspension of 70.8 g potassium carbonate in 480 ml acetone followed by heating to 45° C. Then 63.2 ml dimethylchloromalonate in 50 ml acetone were added within 20 min. The reaction mixture was heated to reflux for 16 h. The solvent was evaporated under reduced pressure, the residue taken into water and extracted with DCM. The combined organic layers were dried over sodium sulfate and evaporated. The oily product was crystallized from methyl-tert.-butyl-ether. 86 g dimethyl-(o-methoxyphenoxy)malonate was obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 h
  3. customThe solvent was evaporated under reduced pressure
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. customevaporated
  7. customThe oily product was crystallized from methyl-tert.-butyl-ether

Sources & evidence

ORD record
ord-7f566953f0cc45148e6fe765b5e1e5ae
Source dataset
uspto-grants-2004_04
Patent number
US06720322B2

Reaction notes

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