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

HRID 2118657Notes

Reaction equation

HRID 2118657 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]OS(C1C=CC(C)=CC=1)(=O)=O.CN(C)C=O>O>[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 70051-NaphtholHCID 11430Potassium CarbonateHCID 139572728-Chlorooctyl 4-methylbenzene-1-sulfonate

Product 1

HCID 139572731-(1-Naphthyloxy)-8-chlorooctane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-naphthol (12.9 g), potassium carbonate (23.5 g), 1-chloro-8-(p-toluenesulphonyloxy)octane (23.5 g) and dimethylformamide (200 ml) was stirred at 55° for 2-1/2 days. The solution was then cooled and added to water, and extracted with ether. The extract was dried and evaporated and the residue was chromatographed on silica gel (750 g), eluting with 3:1 hexane: methylene chloride, so as to afford the title compound as an oil.

Workup

  1. temperatureThe solution was then cooled
  2. extractionextracted with ether
  3. customThe extract was dried
  4. customevaporated
  5. customthe residue was chromatographed on silica gel (750 g)
  6. washeluting with 3:1 hexane

Sources & evidence

ORD record
ord-24fd79f2ef954a1faeb1c247c54357ad
Source dataset
uspto-grants-1987_07
Patent number
US04680300

Reaction notes

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