Sodium Methoxide → HCID 54180592, compound

HRID 259619Notes

Reaction equation

HRID 259619 reaction equation
[C:1]([NH:4][CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14](=O)[CH2:15][O:16][CH3:17])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[CH3:19][O-:20].[Na+]>CO>[C:1]([NH:4][CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:15]2[O:16][CH2:17]2)=[C:9]([O:20][CH3:19])[CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68117788HCID 68117788, compound

Product 1

HCID 54180592HCID 54180592, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

7.5 g (0.03 mol) of 4-(2-acetylaminovinyl)-2-methoxyacetoxybenzene are suspended in 60 ml of absolute methanol a solution of 1.65 g (0.03 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 sodium salt of 4-(2-acetylaminovinyl)-2-methoxy-phenol is heated to the boil with 40 ml of epichlorohydrin for 18 hours whilst stirring and under a reflux condenser. Thereafter the excess epichlorohydrin is removed by distillation under reduced pressure. 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 ethyl acetate, 1-[4-(2-acetylaminovinyl)-2-methoxy-phenoxy]-2,3-epoxy-propane of melting point 173°-174° C. is obtained.

Workup

  1. additionis added
  2. customIt is then evaporated to dryness in vacuo
  3. temperatureThe resulting crude sodium salt of 4-(2-acetylaminovinyl)-2-methoxy-phenol is heated to the boil with 40 ml of epichlorohydrin for 18 hours
  4. customThereafter the excess epichlorohydrin is removed by distillation under reduced pressure
  5. customThe residue is partitioned between water and methylene chloride
  6. customthe organic phase is separated off
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customAfter crystallisation of the crude product

Sources & evidence

ORD record
ord-6ce03a69aeee405baf564a01859445ea
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

Loading…