2-Phenylethanol → [2-[(6-Bromohexyl)oxy]ethyl]benzene

HRID 1534898

Reaction equation

HRID 1534898 reaction equation
[CH2:1]([OH:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 60542-PhenylethanolHCID 123681,6-DibromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 13375574[2-[(6-Bromohexyl)oxy]ethyl]benzeneYield 55.7%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of phenethyl alcohol (20 g), 1,6-dibromohexane (195 g) and tetrabutylammonium bisulphate (3.0 g) in 50% w/v NaOH solution (100 ml) was heated at 65°-70° for 4 h. The cooled reaction mixture was poured into H2O (400 ml) and extracted with CX (2×300 ml). The dried extracts were evaporated in vacuo to give a yellow liquid which was purified by distillation under reduced pressure to give the title compound as a colourless liquid (26 g) b.p. 110°/0.1 mm. T.l.c. (EA) Rf 0.62.

Workup

  1. temperaturewas heated at 65°-70° for 4 h
  2. customThe cooled reaction mixture
  3. extractionextracted with CX (2×300 ml)
  4. customThe dried extracts were evaporated in vacuo
  5. customto give a yellow liquid which
  6. distillationwas purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-fda4490279cd478fa7e5720045c6e2ce
Source dataset
uspto-grants-1992_02
Patent number
US05091422

Linked notes

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