Epichlorohydrin → HCID 4835626, compound

HRID 2166515Notes

Reaction equation

HRID 2166515 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([CH:21]1[O:23][CH2:22]1)Cl>CC(C)=O>[O:23]1[CH2:22][CH:21]1[CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 8434EthylparabenHCID 11430Potassium Carbonate

Product 1

HCID 4835626HCID 4835626, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 16.7 gm (0.10 mole) of ethyl 4-hydroxybenzoate, 20.7 gm (0.15 mole) of potassium carbonate and 24 mL (0.30 mole) of epichlorohydrin in 250 mL acetone was heated to reflux for 12 hours. The reaction medium was then filtered and evaporated. The resulting oil was taken up in 100 mL toluene and washed with 100 mL 1.0 N sodium hydroxide and 2×100 mL water. The toluene phase was then dried over magnesium sulfate and evaporated to give 13.5 gm (61%) of a clear oil. The NMR spectrum of this oil was consistent with the assigned structure and the oil was used in the next reaction step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. filtrationThe reaction medium was then filtered
  4. customevaporated
  5. washwashed with 100 mL 1.0 N sodium hydroxide and 2×100 mL water
  6. dry with materialThe toluene phase was then dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-a31995213aee41f2aeef954adcbe6bdb
Source dataset
uspto-grants-1983_06
Patent number
US04387103

Reaction notes

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