2-Phenylethanol → {2-[(Prop-2-yn-1-yl)oxy]ethyl}benzene

HRID 2166153Notes

Reaction equation

HRID 2166153 reaction equation
[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:11][C:12]#[CH:13].[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:13]([O:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:12]#[CH:11]

Participants

6

Reactant 3

HCID 60542-PhenylethanolHCID 7842Propargyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 12407536{2-[(Prop-2-yn-1-yl)oxy]ethyl}benzene

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of benzenethanol (12.2 g), 3-bromo-1-propyne (12.0 ml), 40% aqueous sodium hydroxide (20 ml) and tetrabutylammonium bisulphate (1 g) was stirred overnight. Water (100 ml) was added and the mixture was extracted with ER (2×100 ml). The organic extracts were washed with water and brine, dried and concentrated to a dark oil which was purified by FCC eluting with CX-ER (19:1) to give the title compound as a pale yellow oil (12.3 g) T.l.c. (CX-ER 19:1) Rf 0.50.

Workup

  1. extractionthe mixture was extracted with ER (2×100 ml)
  2. washThe organic extracts were washed with water and brine
  3. customdried
  4. concentrationconcentrated to a dark oil which
  5. customwas purified by FCC
  6. washeluting with CX-ER (19:1)

Sources & evidence

ORD record
ord-9d5de72653a546c8983ca8ccfe835b36
Source dataset
uspto-grants-1990_07
Patent number
US04943591

Reaction notes

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