Methylparaben → methyl 4-(oxiran-2-ylmethoxy)benzoate

HRID 1981644Notes

Reaction equation

HRID 1981644 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.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:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 7835EpichlorohydrinHCID 11430Potassium Carbonate

Product 1

HCID 2771933methyl 4-(oxiran-2-ylmethoxy)benzoateYield 67.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 15.2 gm (0.1 mole) of methyl 4-hydroxybenzoate, 27.6 gm (0.2 mole) potassium carbonate and 31 mL (0.4 mole) epichlorohydrin in 250 mL acetone was heated to reflux for 24 hours. The reaction medium was then filtered and evaporated. The residue was taken up in 100 mL toluene and washed with 100 mL 1.0N NaOH and 2×100 mL water. The toluene phase was then dried over magnesium sulfate and evaporated to provide the crude product as an oil. Purification was effected by vacuum distillation (66°-67°; 75 u pressure) and provided 14 gm (67%) of a clear oil when gradually crystallized at room temperature: mp 54°-55° C. The NMR and IR spectra and elemental analysis data 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
  5. washwashed with 100 mL 1.0N NaOH and 2×100 mL water
  6. dry with materialThe toluene phase was then dried over magnesium sulfate
  7. customevaporated
  8. customto provide the crude product as an oil
  9. customPurification
  10. distillationwas effected by vacuum distillation (66°-67°; 75 u pressure)

Sources & evidence

ORD record
ord-9a9a168d71224b78ace01aa145a9e338
Source dataset
uspto-grants-1986_06
Patent number
US04593119

Reaction notes

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