Epichlorohydrin → 2-{[(4-Chloronaphthalen-1-yl)oxy]methyl}oxirane

HRID 1390611Notes

Reaction equation

HRID 1390611 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.Cl[CH2:14][CH:15]1[CH2:17][O:16]1.[OH-].[K+]>O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:14][CH:15]2[CH2:17][O:16]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 117874-Chloro-1-naphtholHCID 14797Potassium Hydroxide

Product 1

HCID 57435422-{[(4-Chloronaphthalen-1-yl)oxy]methyl}oxirane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 44.5 parts of 4-chloro-1-naphthalenol and 115 parts of 2-(chloromethyl)oxirane are added portionwise 17.1 parts of potassium hydroxide (exothermic reaction). When the exothermic reaction is ceased, the whole is heated to reflux and stirred at reflux temperature for 2 hours. Water is added and the whole is extracted twice with trichloromethane. The combined extracts are washed three times with water, dried and evaporated. The residue is distilled, yielding 45.3 parts of 2-[(4-chloro-1-naphthalenyloxy)-methyl]oxirane; bp. 150°-151° C. at 0.2 mm. pressure.

Workup

  1. customWhen the exothermic reaction
  2. temperaturethe whole is heated
  3. temperatureto reflux
  4. temperatureat reflux temperature for 2 hours
  5. extractionthe whole is extracted twice with trichloromethane
  6. washThe combined extracts are washed three times with water
  7. customdried
  8. customevaporated
  9. distillationThe residue is distilled

Sources & evidence

ORD record
ord-8f20ce3e32a84aab9f34bf5d0fc97496
Source dataset
uspto-grants-1979_02
Patent number
US04139540

Reaction notes

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