Propargyl alcohol → HCID 13375622, compound

HRID 893764Notes

Reaction equation

HRID 893764 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].Br[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:4][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]#[CH:3]

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 14798Sodium HydroxideHCID 2596681-Bromo-4-phenylbutane

Product 1

HCID 13375622HCID 13375622, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of propargyl alcohol (10.0 g), (4-bromobutyl)benzene (38.0 g), aqueous NaOH (80 ml, 50% w/v), and tetrabutylammonium bisulphate (1.0 g) was stirred vigorously for 3 days, treated with H2O (100 ml) and extracted with ER (2×200 ml). The dried extract was evaporated and the residue was purified on a column of silica (Merck 9385; 500 ml) [H] to give the title compound as a colorless oil (18.3 g). T.l.c. [A] Rf 0.2.

Workup

  1. extractionextracted with ER (2×200 ml)
  2. extractionThe dried extract
  3. customwas evaporated
  4. customthe residue was purified on a column of silica (Merck 9385; 500 ml) [H]

Sources & evidence

ORD record
ord-b61a35f30ce4455aada833339fa7a2fc
Source dataset
uspto-grants-1992_06
Patent number
US05126375

Reaction notes

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