Epichlorohydrin → HCID 3149434, compound

HRID 1892031Notes

Reaction equation

HRID 1892031 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[OH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[CH:17]=[O:18]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:1]([O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[CH:17]=[O:18])[CH:3]1[O:5][CH2:4]1

Participants

5

Reactant 2

HCID 7835Epichlorohydrin2×HCID 128192-Hydroxy-1-naphthaldehyde

Product 1

HCID 3149434HCID 3149434, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6212ChloroformSolvent

Procedure

As shown in Chemical Formula 2, in 196 mL (2.47 mol) of epichlorohydrin (2), 17.1 g (99.0 mmol) of 2-hydroxy-1-naphthoaldehyde (1) was dissolved and thereto, 2.26 g (9.92 mmol) of benzyltriethylammonium chloride was added, followed by refluxing the resultant reaction mixture for 15 minutes to effect the reaction. Then, the reaction solution was dissolved in 200 mL of chloroform and the resultant solution was washed with 150 mL of water three times. The organic phase was dried over MgSO4 (magnesium sulfate), and the solvent thereof was concentrated under reduced pressure. The resultant residue was recrystallized in isopropyl alcohol and the resultant needle crystal was washed with isopropyl alcohol to obtain 16.1 g (yield: 71%) of 2-(glycidyloxy)-1-naphthoaldehyde (3) as a needle crystal.

Workup

  1. temperatureby refluxing the resultant
  2. customreaction mixture for 15 minutes
  3. customthe reaction
  4. washthe resultant solution was washed with 150 mL of water three times
  5. dry with materialThe organic phase was dried over MgSO4 (magnesium sulfate)
  6. concentrationthe solvent thereof was concentrated under reduced pressure
  7. customThe resultant residue was recrystallized in isopropyl alcohol
  8. washthe resultant needle crystal was washed with isopropyl alcohol

Sources & evidence

ORD record
ord-1345f531cf07493c9db467c7838edbbc
Source dataset
uspto-grants-2013_08
Patent number
US08507611B2

Reaction notes

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