Water → Naphthalene, 2-butoxy-

HRID 1767430Notes

Reaction equation

HRID 1767430 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].[OH-].[Na+].[CH2:14](Br)[CH2:15][CH2:16][CH3:17].O>C(O)C>[CH2:14]([O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 86632-NaphtholHCID 14798Sodium Hydroxide2×

Product 1

HCID 82664Naphthalene, 2-butoxy-Yield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 100 g of ethanol were dissolved 50 g (0.347 mol) of 2-naphthol and 14.6 g (0.364 mol) of sodium hydroxide. Under reflux, 50 g (0.364 mol) of n-butyl bromide was added to the solution, which was refluxed for a further 4 hours. To the reaction solution were added 200 g of water and 4 g of sodium hydroxide. The organic layer thus separated, 75 g, was distilled in vacuo, obtaining 59 g of 2-n-butoxynaphthalene. The distillate (liquid) solidified when allowed to stand at room temperature.

Workup

  1. temperatureUnder reflux
  2. temperaturewas refluxed for a further 4 hours
  3. customThe organic layer thus separated
  4. distillation75 g, was distilled in vacuo

Sources & evidence

ORD record
ord-e52eb9556a4640bf89ba07ae17eb57b1
Source dataset
uspto-grants-2007_06
Patent number
US07235343B2

Reaction notes

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