Guaiacol → Diethyl (2-methoxyphenoxy)propanedioate

HRID 1493969Notes

Reaction equation

HRID 1493969 reaction equation
[Na].[C:2]1([O:9][CH3:10])[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:11]([O:13][C:14](=[O:22])[CH:15](Cl)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:12]>C(O)C>[CH2:11]([O:13][C:14](=[O:22])[CH:15]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[O:9][CH3:10])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:12]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 84182Diethyl chloromalonateHCID 5360545Sodium

Product 1

HCID 11140560Diethyl (2-methoxyphenoxy)propanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of 6.9 g (0.3 mole) of sodium pellets dissolved in 400 ml of absolute ethanol was successively added a solution of 37.9 g (0.305 mole) of guaiacol in 50 ml of ethanol followed by a solution of 68.1 g(0.35 mole) of diethylchloromalonate in 50 ml of ethanol. The mixture was heated at reflux for 28 hr and then stirred at ambient temperature for 3 days. The mixture was filtered and the filtrate was concentrated. The residue was partitioned between salt water and ethyl ether. The layers were separated and the aqueous layer was extracted twice with 150 ml portions of ethyl ether. The combined organic layers were washed with brine, dried (sodium sulfate) and concentrated to give a yellow oil. The oil was subjected to vacuum distillation and 66.6 g (79%) of the title compound was collected as a clear oil, bp 136°-153° C. at 0.3 mm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 28 hr
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was partitioned between salt water and ethyl ether
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted twice with 150 ml portions of ethyl ether
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried (sodium sulfate)
  10. concentrationconcentrated
  11. customto give a yellow oil
  12. distillationThe oil was subjected to vacuum distillation and 66.6 g (79%) of the title compound
  13. customwas collected as a clear oil, bp 136°-153° C. at 0.3 mm

Sources & evidence

ORD record
ord-6114c282a1bb45cfb0fb8106d54b8f83
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Reaction notes

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