Diethyl Ether → HCID 22219098, compound

HRID 1767436Notes

Reaction equation

HRID 1767436 reaction equation
C[O-:2].[Na+].[CH2:4]([C:7]1[CH:8]=[C:9]([OH:14])[C:10](=[CH:12][CH:13]=1)[OH:11])[CH:5]=[CH2:6].Br[CH2:16][C:17]([O:19][CH3:20])=[O:18].[CH3:21][CH2:22][O:23][CH2:24][CH3:25]>CO>[CH2:4]([C:7]1[CH:13]=[CH:12][C:10]([O:11][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:9]([O:14][CH2:21][C:22]([O:23][CH2:24][CH3:25])=[O:2])[CH:8]=1)[CH:5]=[CH2:6]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 60984Methyl bromoacetate3×HCID 70775HydroxychavicolHCID 10942334Sodium Methoxide2×

Product 1

HCID 22219098HCID 22219098, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12.8 g (225 mmol) of 95% pure sodium methoxide were introduced into a solution of 16.8 g (112 mmol) of 4-allylcatechol in 250 ml of methanol, with stirring, followed by 21 ml (225 mmol) of methyl bromoacetate. After refluxing for 8 h, a further 21 ml (225 mmol) of methyl bromoacetate were added, and, after a further 4 h of heating, a further 12.8 g (225 mmol) of sodium methoxide and a further 21 ml (225 mmol) of methyl bromoacetate. After a further 4 h under reflux, the mixture was worked up by adding 500 ml of ether and filtering off the precipitate formed. The filtrate was concentrated on a rotary evaporator and taken up in ether/water/saturated ammonium chloride solution (1:1:1). The organic phase was separated off, and the aqueous phase was extracted three times, each time with 200 ml of ether. The combined organic phases were dried over sodium sulfate and concentrated to dryness on a rotary evaporator. After flash chromatography (ether/pentane, 1:1, Rf=0.35) on silica gel, 21.4 g (65%) of methyl 4-allyl-2-(ethoxycarbonylmethoxy)phenoxyacetate were obtained.

Workup

  1. temperatureAfter refluxing for 8 h
  2. temperatureafter a further 4 h of heating
  3. temperatureAfter a further 4 h under reflux
  4. filtrationfiltering off the precipitate
  5. customformed
  6. concentrationThe filtrate was concentrated on a rotary evaporator
  7. customThe organic phase was separated off
  8. extractionthe aqueous phase was extracted three times
  9. dry with materialThe combined organic phases were dried over sodium sulfate
  10. concentrationconcentrated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-b2078e80ae38447ca382587edf92a72e
Source dataset
uspto-grants-2007_06
Patent number
US07235519B2

Reaction notes

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