Styrene → 2-(Chloromethoxy)naphthalene

Temperature

80 °C

4-Chloro-1-(chloromethylthio)benzene (20 mmol) in DMF (10 ml) was added to a mixture of 2-hydroxynaphthalene (20 mmol) and potassium tert-butoxide (20 mmol) in DMF (40 ml). The mixture was stirred at 80° C. for 2 hours before the solvent was distilled off and the residue triturated with water, extracted into ether and washed three times with water. The dried (MgSO4) solution was evaporated and recrystallized from EtOH yield: 3.30 g (57%). m.p. 70° C. The product (10.3 mmol) was dissolved in dry CH2Cl2 (30 ml) and SO2Cl2 (10.3 mmol) in dry CH2Cl2 (10 ml) was added with stirring at room temperature for 5 minutes. The mixture was stirred for 10 minutes before styrene (10.3 mmol) in dry CH2Cl2 (10 ml) was added with stirring at 5° C. for 10 minutes. The mixture was stirred for 20 minutes at room temperature before the solvent was distilled off and the residue distilled under vacuum. Yield: 1.50 g (76%) b.p. 82°-95° C. 0.03 mmHg [see J. Appl. Chem. 3, 266(1953) b.p. 90°-110° C./0.15 mmHg].

1. distillationwas distilled off
2. customthe residue triturated with water
3. extractionextracted into ether
4. washwashed three times with water
5. dry with materialThe dried (MgSO4) solution
6. customwas evaporated
7. customrecrystallized from EtOH yield: 3.30 g (57%)
8. stirringwith stirring at room temperature for 5 minutes
9. additionwas added
10. stirringwith stirring at 5° C. for 10 minutes
11. stirringThe mixture was stirred for 20 minutes at room temperature before the solvent
12. distillationwas distilled off
13. distillationthe residue distilled under vacuum

ORD record

ord-584f78408caa420d943e9a4209dfc234

Source dataset

uspto-grants-1987_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04705791