Dimethylformamide → 1-(2-Naphthyloxy)-8-chlorooctane

HRID 485300Notes

Reaction equation

HRID 485300 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].C1(C)C=CC(S(O[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Cl:30])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CCOCC.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][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Cl:30]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 86632-NaphtholHCID 11430Potassium CarbonateHCID 139572728-Chlorooctyl 4-methylbenzene-1-sulfonate

Product 1

HCID 135205391-(2-Naphthyloxy)-8-chlorooctane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-naphthol (17.5 g), 1-(p-toluenesulphonyloxy)-8-chlorooctane (32.0 g), anhydrous potassium carbonate (32.0 g) and dimethylformamide (200 ml) was stirred at 60° for 4 hours. Water and ether were then added, and the ethereal solution was washed with water and dilute aqueous potassium hydroxide, then dried and evaporated. The residue was chromotographed on silica gel, eluting with 3:2 hexane:dichloromethane, to afford the title compound as a solid, mp 35°.

Workup

  1. washthe ethereal solution was washed with water and dilute aqueous potassium hydroxide
  2. customdried
  3. customevaporated
  4. washeluting with 3:2 hexane

Sources & evidence

ORD record
ord-900b0bf7f81e4a29bbbf1077fe4da1c3
Source dataset
uspto-grants-1985_08
Patent number
US04536503

Reaction notes

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