Epichlorohydrin → Methyl 3-{4-[(oxiran-2-yl)methoxy]phenyl}propanoate

HRID 544421Notes

Reaction equation

HRID 544421 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl>CC(C)=O>[O:24]1[CH2:23][CH:22]1[CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Product 1

HCID 13040891Methyl 3-{4-[(oxiran-2-yl)methoxy]phenyl}propanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 228 gm (1.27 mole) of methyl 3-(4-hydroxyphenyl)propionate, 263 gm (1.90 mole) of K2CO3 and 298 mL (3.80 mole) of epichlorohydrin in 2 liters of acetone was stirred and heated to reflux for 20 hours. The reaction medium was then filtered and evaporated under reduced pressure. The resulting oil was taken up in 1 liter of toluene andwashed consecutively with 500 mL water, 2×500 mL 1N NaOH and 2×500 mL water. The toluene phase was then dried over MgSO4 andevaporated under reduced pressure to provide a clear oil which was further purified by vacuum distillation. The final yield of purified oil was 131.2gm (44%): bp 156° (p=0.4 mm Hg). The NMR and IR spectra of the product were consistent with the assigned structure and the elemental analysis was consistent with the formula C13H16O4.

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 hours
  3. filtrationThe reaction medium was then filtered
  4. customevaporated under reduced pressure
  5. dry with materialThe toluene phase was then dried over MgSO4
  6. customto provide a clear oil which
  7. distillationwas further purified by vacuum distillation

Sources & evidence

ORD record
ord-5ecc9b4ba92c4e4d81a9c47069ab1d40
Source dataset
uspto-grants-1984_05
Patent number
US04450173

Reaction notes

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