1,5-Dihydroxynaphthalene → HCID 14814248, compound

HRID 1613566Notes

Reaction equation

HRID 1613566 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:13]2[C:8](=[C:9]([OH:14])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.[CH2:15](I)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(O)C>[CH2:15]([O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[OH:14])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 67491,5-DihydroxynaphthaleneHCID 14798Sodium HydroxideHCID 163141-Iododecane

Product 1

HCID 14814248HCID 14814248, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12 g (0.3 Mol) sodium hydroxide are dissolved while heating in 500 ml ethanol and a solution of 25 g (0.15 Mol) 1,5-dihydroxynaphthalene 97% is added to the cooled solution within 20 minutes. Afterwards 40.23 g (0.15 Mol) n-decyl iodide is added dropwise within 20 minutes and it is subsequently boiled for 4 hours under reflux. After aspiration of the inorganic residue, the filtrate is concentrated in a vacuum and the dark-brown, semi-crystalline residue is purified by column chromatography on silica gel 60 (Merck). Mobile solvent: toluol/methanol=7:1. After recrystallization from n-heptane the corresponding eluate yields 11.5 g (25.3% of the theroretical yield) product, light-brown crystals, Fp 85°-87° C.

Workup

  1. temperatureunder reflux
  2. concentrationAfter aspiration of the inorganic residue, the filtrate is concentrated in a vacuum
  3. customthe dark-brown, semi-crystalline residue is purified by column chromatography on silica gel 60 (Merck)
  4. customAfter recrystallization from n-heptane the corresponding
  5. customeluate yields 11.5 g (25.3% of the
  6. customtheroretical yield) product, light-brown crystals, Fp 85°-87° C.

Sources & evidence

ORD record
ord-fc790a566e1d4c9bb33aa6b1a634af7d
Source dataset
uspto-grants-1993_03
Patent number
US05194389

Reaction notes

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