2-Naphthol → HCID 14856822, compound

HRID 2051887Notes

Reaction equation

HRID 2051887 reaction equation
[H-].[Na+].CN(C)P(N(C)C)(N(C)C)=O.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[OH:24].Cl[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32]>O>[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[O:24][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32]

Participants

6

Reactant 4

HCID 86632-NaphtholHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 748286-Chloro-1-hexanol

Product 1

HCID 14856822HCID 14856822, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a chilled round bottom flask is added, 4.2 g of 57% sodium hydride in oil, 50 ml of hexamethylphosphoramide and 15.8 g. of 2-naphthol. After 1/2 hour the mixture is allowed to warm to room temperature and 13.6 g. of 6-chlorohexan-1-ol is added. The mixture is heated at 110° C. overnight, cooled, diluted with water and extracted with ether. The ether extract is washed with sodium hydroxide solution, then with water, dried (magnesium sulfate) and the solvent removed under vacuum. The solid is dissolved in ether and the solution washed with sodium hydroxide solution. The ether layer is dried (magnesium sulfate) and the solvent removed under vacuum to give 15.9 g. of product, as crystals, mp 53°-56° C.

Workup

  1. additionTo a chilled round bottom flask is added
  2. temperatureThe mixture is heated at 110° C. overnight
  3. temperaturecooled
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washis washed with sodium hydroxide solution
  7. dry with materialwith water, dried (magnesium sulfate)
  8. customthe solvent removed under vacuum
  9. dissolutionThe solid is dissolved in ether
  10. washthe solution washed with sodium hydroxide solution
  11. dry with materialThe ether layer is dried (magnesium sulfate)
  12. customthe solvent removed under vacuum
  13. customto give 15.9 g

Sources & evidence

ORD record
ord-e305e7fc770a4144aea9a420715a73e4
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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