Guaiacol → Dimethyl 2-(2-methoxyphenoxy)malonate

HRID 8600

Reaction equation

HRID 8600 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

2-methoxy-phenol (guaiacol) (48 ml) was slowly added to a stirred suspension of potassium carbonate (70.8 g) in acetone (480 ml) followed by heating to 45° C. Then dimethylchloromalonate (63.2 ml) in acetone (50 ml) was 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 to give dimethyl-(2-methoxyphenoxy)malonate (86 g).

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-442b1ca72e0741b6b6941fed4e97a70d
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Linked notes

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