Diethyl Ether → 2-((1-Naphthalenyloxy)methyl)oxirane

HRID 376912Notes

Reaction equation

HRID 376912 reaction equation
[H-].[Na+].[C:3]1([OH:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl.C(OCC)C>CN(C)C=O.O>[CH2:14]([O:13][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)[CH:16]1[O:18][CH2:17]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 70051-NaphtholHCID 7835EpichlorohydrinHCID 24758Sodium hydride

Product 1

HCID 915212-((1-Naphthalenyloxy)methyl)oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred suspension of sodium hydride (4.0 g of 60% NaH in mineral oil, 100 mmol) in dimethylformamide (DMF, 100 ml) was treated with 1-naphthol (14.42 g, 100 mmol). After stirring for 1 hour at ambient temperature (room temperature), the reaction was treated with epichlorohydrin (10.18 g, 110 mmol) and stirred for 1 hour at 100° C. The reaction was diluted with water and transferred to a separatory funnel using diethyl ether (500 ml). The organic phase was washed with 10% aqueous NaHCO3 (3×200 ml), dried over anhydrous sodium sulfate, filtered, and concentrated. Kugelrohr distillation (~100 microns) yielded 1-naphthyl glycidyl ether as a clear, colorless oil: GC/EI-MS, m/z (rel. int.) 200 (M+, 61), 184 (1), 169 (5), 157 (12), 144 (79), 129 (16), 115 (100), 101 (3), 89 (16).

Workup

  1. stirringstirred for 1 hour at 100° C
  2. customtransferred to a separatory funnel
  3. washThe organic phase was washed with 10% aqueous NaHCO3 (3×200 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationKugelrohr distillation (~100 microns)

Sources & evidence

ORD record
ord-3ff35f1e5b2845aca56fea04ded66e1d
Source dataset
uspto-grants-2000_02
Patent number
US06022894

Reaction notes

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