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

HRID 2118660Notes

Reaction equation

HRID 2118660 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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>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][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][Cl:12]

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

Workup

  1. customthe ethereal solution was separated
  2. washwashed with water and dilute aqueous potassium hydroxide
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 3:2 hexane

Sources & evidence

ORD record
ord-32f52dab365044f99921d7d1dfd0cd84
Source dataset
uspto-grants-1987_07
Patent number
US04680300

Reaction notes

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