1-Naphthol → 2-((1-Naphthalenyloxy)methyl)oxirane

HRID 1773003Notes

Reaction equation

HRID 1773003 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.[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl>CS(C)=O>[C:1]1([O:11][CH2:12][CH:14]2[CH2:15][O:16]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70051-NaphtholHCID 7835Epichlorohydrin

Product 1

HCID 915212-((1-Naphthalenyloxy)methyl)oxiraneYield 81.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-naphthol (3.0 g, 0.02 mol) in DMSO (10 mL), potassium hydroxy (flakes, 2.0 g, 0.06 mol) was added. The combined mixture was stirred at room temperature for 30 min and then epichlorohydrin (5.6 g, 4.7 mL, 0.06 mol) was added slowly over a period of 45 min and stirring was continued for 16 hours. The reaction was quenched with water (30 mL) and extracted with chloroform (2×50 mL). The combined organic layers were washed with 1N aqueous NaOH (2×50 mL), water (2×100 mL) and brine (2×100 mL) and dried over MgSO4. The solvent was removed under reduced pressure to provide Compound 1 as a yellow liquid (3.26 g, 78%). This product was used without further purification. The structure of Compound 1 is given below:

Workup

  1. stirringstirring
  2. waitwas continued for 16 hours
  3. customThe reaction was quenched with water (30 mL)
  4. extractionextracted with chloroform (2×50 mL)
  5. washThe combined organic layers were washed with 1N aqueous NaOH (2×50 mL), water (2×100 mL) and brine (2×100 mL)
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e4bed7a9b0ba48388c3b59ca465fecf7
Source dataset
uspto-grants-2016_02
Patent number
US09250249B2

Reaction notes

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