Epichlorohydrin → HCID 13420181, compound

HRID 1380583Notes

Reaction equation

HRID 1380583 reaction equation
[Mg].[C:2]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Cl)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl>CCOCC>[C:2]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10][CH2:14][CH:16]2[O:18][CH2:17]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 88198Benzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-HCID 5462224Magnesium

Product 1

HCID 13420181HCID 13420181, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
80 °C

Procedure

A Grignard solution freshly prepared from 12.15 g (0.50 gram atom) magnesium chips and 91.7 g (0.50 mole) 4-tert.-butylbenzyl chloride in 550 ml dry ether is dripped with agitation into a precooled solution of 92.5 g (1.00 mole) epichlorohydrin in 165 ml dry ether, so that the temperature does not exceed -40° C. After addition is complete, the cooling bath is removed, the solution is allowed to stand for several hours at room temperature, and then hydrolyzed with ice water and dilute hydrochloric acid. The ether phase is separated, washed with water and dried over sodium sulfate. After the ether has been drawn off, the bath temperature is raised to 80° C. and the volatile components carefully removed at 0.1 mbar. The residue is taken up in 270 ml methanol and a freshly prepared solution of 6.90 g (0.30 g atom) sodium in 200 ml methanol added at room temperature. After three hours the sodium chloride precipitated is separated, the filtrate concentrated in vacuum, the residue taken up in ether and washed with water. After drying over sodium sulfate the solvent is removed and the oily residue distilled in vacuum. A colorless liquid with a boiling point of 79°-81° C./0.1 mbar is obtained.

Workup

  1. customdoes not exceed -40° C
  2. additionAfter addition
  3. customthe cooling bath is removed
  4. waitto stand for several hours at room temperature
  5. customThe ether phase is separated
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  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 200 ml methanol added at room temperature
  10. customAfter three hours the sodium chloride precipitated
  11. customis separated
  12. concentrationthe filtrate concentrated in vacuum
  13. washwashed with water
  14. dry with materialAfter drying over sodium sulfate the solvent
  15. customis removed
  16. distillationthe oily residue distilled in vacuum
  17. customA colorless liquid with a boiling point of 79°-81° C./0.1 mbar is obtained

Sources & evidence

ORD record
ord-aadbcf6214b3424ba8373a8322160043
Source dataset
uspto-grants-1986_04
Patent number
US04582857

Reaction notes

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