1-Naphthol → 1-(2-Bromoethoxy)naphthalene

HRID 615618

Reaction equation

HRID 615618 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.[OH-].[K+].C1(C([O-])=O)C2C(=CC=CC=2)C=CC=1.[K+].[Br:28][CH2:29][CH2:30]Br>C(O)C>[Br:28][CH2:29][CH2:30][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 70051-NaphtholHCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 23664128Potassium naphthalate

Product 1

HCID 110759061-(2-Bromoethoxy)naphthaleneYield 50.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 144.0 g (1 mole) α-naphthol and 56.1 g (1 mole) potassium hydroxide in 600 ml of 95% ethanol was stirred 1.5 hr at room temperature. To this solution of potassium naphthalate was added 930.0 g (5.0 mole) of 1,2-dibromoethane, and the solution was heated at reflux overnight. The reaction mixture was filtered, and the filtrate stripped to dryness under reduced pressure in a rotary evaporator. The resulting oil was dissolved in chloroform and the solution extracted with 10% aqueous sodium hydroxide. The chloroform layer was dried and stripped of chloroform to yield 126 g (50.3%) of dark brown oil.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate stripped to dryness under reduced pressure in a rotary evaporator
  5. dissolutionThe resulting oil was dissolved in chloroform
  6. extractionthe solution extracted with 10% aqueous sodium hydroxide
  7. dry with materialThe chloroform layer was dried

Sources & evidence

ORD record
ord-e126e237c225482f838909074476a55e
Source dataset
uspto-grants-1985_02
Patent number
US04500529

Linked notes

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