Sodium Methoxide → 1-[p-(2-Methoxycarbonylaminovinyl)-phenoxy]-2,3-epoxypropane

HRID 597644Notes

Reaction equation

HRID 597644 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=O)[CH3:16])=[CH:10][CH:9]=1)=[O:4].[CH3:18][O-:19].[Na+]>CO>[CH3:1][O:2][C:3]([NH:5][CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]2[O:19][CH2:18]2)=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54318859p-(2-Methoxycarbonylaminovinyl)-acetoxybenzene

Product 1

HCID 543618201-[p-(2-Methoxycarbonylaminovinyl)-phenoxy]-2,3-epoxypropane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

6.8 g (0.035 mol) of p-(2-methoxycarbonylaminovinyl)-acetoxybenzene are suspended in 100 ml of absolute methanol, a solution of 1.9 g (0.035 mol) of sodium methoxide in 15 ml of absolute methanol is added and thereafter the mixture is warmed to 50°C for 15 minutes. It is then evaporated to dryness in vacuo. The resulting, crude phenolate of p-(2-methoxycarbonylaminovinyl)-phenol is heated with 35 ml of epichlorohydrin to the boil for 24 hours under a reflux condenser, whilst stirring. Thereafter, the excess epichlorohydrin is removed by vacuum distillation. The residue is partitioned between water and methylene chloride and the organic phase is separated off, dried over sodium sulphate and evaporated. After crystallisation of the crude product thus obtained, from acetone-ether, 1-[p-(2-methoxycarbonylaminovinyl)-phenoxy]-2,3-epoxy-propane of melting point 125°-126°C is obtained.

Workup

  1. customIt is then evaporated to dryness in vacuo
  2. temperatureThe resulting, crude phenolate of p-(2-methoxycarbonylaminovinyl)-phenol is heated with 35 ml of epichlorohydrin to the boil for 24 hours under a reflux condenser
  3. customThereafter, the excess epichlorohydrin is removed by vacuum distillation
  4. customThe residue is partitioned between water and methylene chloride
  5. customthe organic phase is separated off
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customAfter crystallisation of the crude product

Sources & evidence

ORD record
ord-1db5d94ec3c74b2db00f505f8d1688d7
Source dataset
uspto-grants-1977_03
Patent number
US04014920

Reaction notes

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