Epichlorohydrin → HCID 13137383, compound

HRID 1981651Notes

Reaction equation

HRID 1981651 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH3:15])=[O:11])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>CC(C)=O>[O:26]1[CH2:25][CH:24]1[CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH3:15])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 13137381HCID 13137381, compound

Product 1

HCID 13137383HCID 13137383, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 9 g (0.04 mole) of n-propyl 3-(4-hydroxyphenyl)propionate, 10 g (0.08 mole) of K2CO3 and 12 mL (0.15 mole) of epichlorohydrin in 150 mL 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 100 mL toluene and washed consecutively with 50 mL water 2×50 mL of 1N NaOH and 2×50 mL of water. The toluene phase was then dried over MgSO4 and evaporated under reduced pressure to provide 3 g (30%) of a clear oil which was used directly in the next step without additional purification. The IR and NMR spectra of the reaction product were consistent with the assigned structure.

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 hours
  3. filtrationThe reaction medium was then filtered
  4. customevaporated under reduced pressure
  5. washwashed consecutively with 50 mL water 2×50 mL of 1N NaOH and 2×50 mL of water
  6. dry with materialThe toluene phase was then dried over MgSO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bba62eb017a24baf8ee1dfd566f79e91
Source dataset
uspto-grants-1986_06
Patent number
US04593119

Reaction notes

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