Ethanol → 2-((1-Naphthalenyloxy)methyl)oxirane
Reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl.C(O)C>O>[O:18]1[CH:16]([CH2:14][O:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH2:17]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a 500 mL three-necked round bottom flask, 10.03 g 1-naphthol, 3.1 g NaOH, 20.4 g epichlorohydrin (SIR) and 0.5 g KI were added, then 330 mL ethanol was added. The flask was then placed in a microwave reactor. The reaction was performed at 30° C. under stirring and 300 W microwave irradiation for 12 min. The reaction mixture was then removed and suction filtrated, and the filtrate was concentrated to obtain an oily substance. H2O was added to the oily substance, and the mixture was extracted with ethyl ether. The ethyl ether layers were combined and washed with a solution of NaOH, then washed with H2O once. The ether layer was dried using anhydrous magnesium sulfate and concentrated to obtain 12.95 g of the product in a yield of 93.2%.
Workup
- customThe flask was then placed in a microwave reactor
- customwas performed at 30° C.
- custom300 W microwave irradiation for 12 min
- customThe reaction mixture was then removed
- filtrationsuction filtrated
- concentrationthe filtrate was concentrated
- customto obtain an oily substance
- extractionthe mixture was extracted with ethyl ether
- washwashed with a solution of NaOH
- washwashed with H2O once
- dry with materialThe ether layer was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c0f5480cf04f4a3bb2fb3388cfc3a701
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017786B2
Reaction notes
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