1-Bromo-3-chloropropane → 3-(2-Naphthyloxy)-1-chloropropane

HRID 1614621Notes

Reaction equation

HRID 1614621 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[Cl:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:12][CH2:13][CH2:14][CH2:15][O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 86632-NaphtholHCID 11430Potassium Carbonate

Product 1

HCID 116872053-(2-Naphthyloxy)-1-chloropropaneYield 52.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-naphthol (72.07 g, 0.5 mol), 1-chloro-3-bromopropane (78.72 g, 0.5 mol), and potassium carbonate (103.65 g, 0.75 mol) was heated at reflux 16 hr in 750 mL of acetone. The mixture was cooled to room temperature and filtered. The reaction was concentrated to a viscous oil using a rotary evaporator. The oil was dissolved in chloroform and washed with 5% sodium hydroxide and water. The chloroform was dried (Na2SO4) and filtered. Chloroform was removed to give a brown solid. A ten-gram sample was subjected to flash chromatography on silica gel using 2% ethyl acetate-hexanes, 3% ethylacetate-hexanes, 5% ethyl acetate-hexanes, and 10% ethyl acetate-hexanes for elution. Fractions of similar purity were combined and solvents removed. A clear oil was obtained and dried 16 hr at 80° C. A white crystalline solid was formed on standing at room temperature. This procedure provided 7.01 g (52.2%) of white crystalline solid, mp 46°-49° C.

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. concentrationThe reaction was concentrated to a viscous oil
  4. customa rotary evaporator
  5. dissolutionThe oil was dissolved in chloroform
  6. washwashed with 5% sodium hydroxide and water
  7. dry with materialThe chloroform was dried (Na2SO4)
  8. filtrationfiltered
  9. customChloroform was removed
  10. customto give a brown solid
  11. washA ten-gram sample was subjected to flash chromatography on silica gel using 2% ethyl acetate-hexanes, 3% ethylacetate-hexanes, 5% ethyl acetate-hexanes, and 10% ethyl acetate-hexanes for elution
  12. customsolvents removed
  13. customA clear oil was obtained
  14. customdried 16 hr at 80° C
  15. customA white crystalline solid was formed
  16. customon standing at room temperature

Sources & evidence

ORD record
ord-667c122491d940dfb3eb11837ed5f55b
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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