1-Bromooctadecane → 2-(Octadecyloxy)naphthalene

HRID 1613565Notes

Reaction equation

HRID 1613565 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][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(O)C>[CH2:31]([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)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

5

Reactant 3

HCID 82181-BromooctadecaneHCID 86632-NaphtholHCID 14798Sodium Hydroxide

Product 1

HCID 142016802-(Octadecyloxy)naphthalene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

172.8 g (1.2 mol) 2-naphthol (98%) is added to a solution of 48 g (1.2 mol) sodium hydroxide (99%) in 1 l ethanol in a 4 l three-neck flask with stirrer, cooler and thermometer, after it has dissolved 417 g (1.25 mol) n-octadecylbromide are added and the reaction mixture is heated for 14 hours under reflux. After addition of a further 1 l ethanol the hot solution is aspirated over a Seitz filter to remove inorganic material and the weak pink coloured filtrate is brought to crystallization by placing it in an ice bath for 30 minutes. After aspiration of the almost colourless crystals, the filter cake is washed in portions with ca 700 ml ethanol and after drying over diphosphorus pentoxide 371.9 g (93.7% of the theoretical yield) 2-octadecyloxynaphthalene are obtained as colourless crystals, mp 64°-68° C.

Workup

  1. additionare added
  2. temperaturethe reaction mixture is heated for 14 hours
  3. temperatureunder reflux
  4. filtrationfilter
  5. customto remove inorganic material
  6. customthe weak pink coloured filtrate is brought to crystallization
  7. customfor 30 minutes
  8. washAfter aspiration of the almost colourless crystals, the filter cake is washed in portions with ca 700 ml ethanol
  9. dry with materialafter drying over diphosphorus pentoxide 371.9 g (93.7% of the

Sources & evidence

ORD record
ord-b9a0a7acd56540c8a05fa2c4ca92578c
Source dataset
uspto-grants-1993_03
Patent number
US05194389

Reaction notes

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