Hydrochloric Acid → 2-[(4-Ethylphenyl)methyl]oxirane

HRID 1380584Notes

Reaction equation

HRID 1380584 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.Cl>CCOCC>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:11][CH:13]2[O:15][CH2:14]2)=[CH:4][CH:5]=1)[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7835EpichlorohydrinHCID 153131-Bromo-4-ethylbenzeneHCID 5462224Magnesium

Product 1

HCID 233255792-[(4-Ethylphenyl)methyl]oxirane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

A Grignard solution freshly prepared from 12.15 g (0.50 g atom) magnesium chips and 92.5 g (0.50 mole) 1-bromo-4-ethylbenzene in 400 ml dry ether is dripped with agitation into a precooled solution of 92.5 g (1.00 mole) of epichlorohydrin in 100 ml of dry ether, so that the temperature does not exceed -40° C. After addition is complete, the solution is heated slowly to 20° C. and is hydrolyzed after another three hours by the addition of ice water and dilute hydrochloric acid. The ether phase is separated, washed twice with water and dried over sodium sulfate. Following the removal of the ether, the bath temperature is raised to 70° C. and the volatile components carefully removed at 0.1 mbar. The residue is taken up in 185 ml of methanol and a freshly prepared solution of 6.90 g (0.30 g atom) sodium in methanol added at room temperature. After three hours the sodium chloride precipitate is separated, the filtrate concentrated in vacuum and the yellow, oily residue used without purification for further conversion.

Workup

  1. customdoes not exceed -40° C
  2. additionAfter addition
  3. customThe ether phase is separated
  4. washwashed twice with water
  5. dry with materialdried over sodium sulfate
  6. customthe removal of the ether
  7. temperaturethe bath temperature is raised to 70° C.
  8. customthe volatile components carefully removed at 0.1 mbar
  9. additiona freshly prepared solution of 6.90 g (0.30 g atom) sodium in methanol added at room temperature
  10. customAfter three hours the sodium chloride precipitate is separated
  11. concentrationthe filtrate concentrated in vacuum
  12. customthe yellow, oily residue used without purification for further conversion

Sources & evidence

ORD record
ord-a51207bdfb82423c895d29cbedc5ed51
Source dataset
uspto-grants-1986_04
Patent number
US04582857

Reaction notes

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