2-Naphthol → 4-(2-Naphthyloxy)-1-chlorobutane

HRID 1793460Notes

Reaction equation

HRID 1793460 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].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23]>CC(C)=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:19][CH2:20][CH2:21][CH2:22][Cl:23]

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 116587114-(2-Naphthyloxy)-1-chlorobutane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of β-naphthol (1gm, 0.006 mole), anhydrous K2CO3 (10 gm, in excess) and 1-bromo 4-chlorobutane (0.8 ml, 0.006 mole) was refluxed in dry acetone (50 ml) for 6 hours. Reaction mixture was filtered and filtrate was concentrated to get oily compound, which was crystallized with benzene-hexane to give the colorless crystals of pure desired compound, m.p. 112° C., (yield 1.6 gm, 98%).

Workup

  1. customReaction mixture
  2. filtrationwas filtered
  3. concentrationfiltrate was concentrated
  4. customto get oily compound, which
  5. customwas crystallized with benzene-hexane

Sources & evidence

ORD record
ord-75b4cf608c3c4ee085a72555b323ce4b
Source dataset
uspto-grants-2006_07
Patent number
US07081465B2

Reaction notes

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