Methyl Salicylate → Methyl 2-(oxiran-2-ylmethoxy)benzoate

HRID 1981649Notes

Reaction equation

HRID 1981649 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl>CC(C)=O>[O:22]1[CH2:21][CH:20]1[CH2:18][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 7835EpichlorohydrinHCID 11430Potassium Carbonate

Product 1

HCID 279510Methyl 2-(oxiran-2-ylmethoxy)benzoateYield 12%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 15.2 g (0.10 mole) of methyl 2-hydroxybenzoate, 27.6 g (0.20 mole) of K2CO3 and 31 mL (0.40 mole) of epichlorohydrin in 250 mL of acetone was heated to reflux for 24 hours. The reaction medium was then filtered and evaporated under reduced pressure. The resulting oil was dissolved in 100 mL toluene and washed consecutively with 100 mL water, 2×100 mL 1.0N NaOH, and 2×100 mL water. The organic phase was then dried over MgSO4 and evaporated under reduced pressure to provide the crude product as an oil. Purification was effected by vacuum distillation to provide an oil in 12% yield: boiling point 148° C. (75 u). The NMR and IR spectra and elemental analysis were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. filtrationThe reaction medium was then filtered
  4. customevaporated under reduced pressure
  5. dissolutionThe resulting oil was dissolved in 100 mL toluene
  6. washwashed consecutively with 100 mL water, 2×100 mL 1.0N NaOH, and 2×100 mL water
  7. dry with materialThe organic phase was then dried over MgSO4
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-482f4d869f654919b9ff79ce5aebf746
Source dataset
uspto-grants-1986_06
Patent number
US04593119

Reaction notes

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