Epichlorohydrin → 2-(Oxiran-2-ylmethoxy)benzonitrile

HRID 224888Notes

Reaction equation

HRID 224888 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].[CH2:10]([CH:12]1[O:14][CH2:13]1)Cl>N1CCCCC1>[O:14]1[CH2:13][CH:12]1[CH2:10][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 119072-Hydroxybenzonitrile

Product 1

HCID 126196712-(Oxiran-2-ylmethoxy)benzonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

A solution of 2-cyanophenol (25.0 g., 0.21 mole), epichlorohydrin (117 g., 1.26 mole), and piperidine (10 drops) was stirred and heated at 115°-120° in an oil bath for 2 hours. The reaction mixture was then concentrated (90°/30 mm) to remove unreacted epichlorohydrin. The residue was diluted with toluene and taken to dryness twice to help remove the last traces of volatile material. The residual oil was dissolved in 263 ml. of THF, and the solution stirred at 40°-50° for 1 hour with 263 ml. of 1 N NaOH. The organic layer was separated and concentrated to give an oil which was combined with the aqueous phase. The mixture was extracted with CH2Cl2, and the extract dried (MgSO4) and concentrated to give 36.6 g (100%) of oil which slowly crystallized to a waxy solid. This product was used without further purification in Procedure 26A.

Workup

  1. temperatureheated at 115°-120° in an oil bath for 2 hours
  2. concentrationThe reaction mixture was then concentrated (90°/30 mm)
  3. customto remove unreacted epichlorohydrin
  4. additionThe residue was diluted with toluene
  5. customto help remove the last traces of volatile material
  6. dissolutionThe residual oil was dissolved in 263 ml
  7. customThe organic layer was separated
  8. concentrationconcentrated
  9. customto give an oil which
  10. extractionThe mixture was extracted with CH2Cl2
  11. dry with materialthe extract dried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-dadb1b340fe343a98526687eaa1997f2
Source dataset
uspto-grants-1980_11
Patent number
US04234595

Reaction notes

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