Nitrogen → HCID 3630430, compound

HRID 1632294Notes

Reaction equation

HRID 1632294 reaction equation
N#N.[CH2:3]([CH:5]1[O:7][CH2:6]1)Cl.[C:8]1([O:18][CH3:19])[C:9](=[CH:11][CH:12]=[C:13]([CH:17]=1)[CH2:14][CH:15]=[CH2:16])[OH:10].[OH-].[Na+]>>[CH2:3]([O:10][C:9]1[CH:11]=[CH:12][C:13]([CH2:14][CH:15]=[CH2:16])=[CH:17][C:8]=1[O:18][CH3:19])[CH:5]1[O:7][CH2:6]1

Participants

5

Reactant 4

HCID 947Nitrogen2×HCID 3314EugenolHCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide

Product 1

HCID 3630430HCID 3630430, compound

Procedure

A 2,000 mL, 3-necked, round-bottom flask was equipped with a mechanical stirrer, a 250 mL pressure equalizing addition funnel and a reflux condenser. The addition funnel served as the N2 inlet and the reflux condenser served as the N2 outlet. The flask was purged with a vigorous stream of N2 for 10 min. prior to its use. The flask was charged with epichlorohydrin (740 g, 8.0 mol) and eugenol (328 g, 2.0 mol). These were heated to ca. 80° using a heating mantle while stirring at a moderate rate (ca. 500 rpm). The 50% NaOH (168 g, 2.0 mol) was placed in the addition funnel and was added dropwise to the reaction flask over a 3 hour period. The mixture was allowed to cool and was filtered through a Buchner funnel. The epichlorohydrin was removed by rotary evaporation. The residue was taken up in CH2Cl2 (800 mL) and was washed with 10% NaOH (100 mL) brine and dried (Na2SO4). The crude product was vacuum distilled through a 10 cm Vigreux column to yield 4-allyl-2-methoxyphenyl glycidyl ether, i.e., ##STR22##

Workup

  1. customA 2,000 mL, 3-necked, round-bottom flask was equipped with a mechanical stirrer
  2. additionaddition funnel and a reflux condenser
  3. customThe flask was purged with a vigorous stream of N2 for 10 min.
  4. temperatureThese were heated to ca. 80°
  5. additionwas added dropwise to the reaction flask over a 3 hour period
  6. temperatureto cool
  7. filtrationwas filtered through a Buchner funnel
  8. customThe epichlorohydrin was removed by rotary evaporation
  9. washwas washed with 10% NaOH (100 mL) brine
  10. dry with materialdried (Na2SO4)
  11. distillationdistilled through a 10 cm Vigreux column

Sources & evidence

ORD record
ord-11cf2d35e6d748d2805a6c2bf7a5ceb8
Source dataset
uspto-grants-1984_10
Patent number
US04474963

Reaction notes

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