Guaiacol → Dimethyl 2-(2-methoxyphenoxy)malonate

HRID 486637Notes

Reaction equation

HRID 486637 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].Cl[CH:11]([C:16]([O:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13].C[O-].[Na+].[Na]>CO>[CH3:9][O:8][C:1]1[CH:7]=[CH:6][CH:5]=[CH:4][C:2]=1[O:3][CH:11]([C:16]([O:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 120070Dimethyl chloromalonateHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 12967085Dimethyl 2-(2-methoxyphenoxy)malonateYield 77.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

25 g of guaiacol and 37 g of dimethyl chloromalonate were added dropwise in succession to a sodium methylate solution from 150 ml of methanol and 4.6 g of sodium. The suspension was stirred at 45° C. for 1 hour with the exclusion of moisture, thereafter the methanol was distilled off. The residue was taken up in 200 ml of toluene and washed with water, 1% sodium hydroxide solution and water until the organic phase was colorless. After drying and evaporating the solvent, the residue was distilled. There were obtained 39.5 g of dimethyl (o-methoxyphenoxy)malonate. B.p. 128° C./7 Pa.

Workup

  1. distillationthe methanol was distilled off
  2. washwashed with water, 1% sodium hydroxide solution and water until the organic phase
  3. customAfter drying
  4. customevaporating the solvent
  5. distillationthe residue was distilled

Sources & evidence

ORD record
ord-b5051a395a1b429284d117628bdc1782
Source dataset
uspto-grants-1994_03
Patent number
US05292740

Reaction notes

Loading…