3-Butyn-1-OL → HCID 20071329, compound

HRID 568868Notes

Reaction equation

HRID 568868 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].Br[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>O>[CH2:1]([O:5][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][C:3]#[CH:4]

Participants

5

Reactant 3

HCID 135663-Butyn-1-OLHCID 14798Sodium HydroxideHCID 2596681-Bromo-4-phenylbutane

Product 1

HCID 20071329HCID 20071329, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-butyn-1-ol (5.0 g), (4-bromobutyl)benzene (15.0 g), aqueous sodium hydroxide (30 ml, 50% w/v), and TAB (0.6 g) was stirred vigorously for 3 days, treated with water (100 ml) and extracted with ER (2×200 ml). The dried extract was evaporated and the residue was purified by FCC eluting with CX-ER 19:1 to give the title compound as a colourless oil (9.5 g). T.l.c. (CX-ER 9:1) Rf 0.45.

Workup

  1. extractionextracted with ER (2×200 ml)
  2. extractionThe dried extract
  3. customwas evaporated
  4. customthe residue was purified by FCC
  5. washeluting with CX-ER 19:1

Sources & evidence

ORD record
ord-cf12bc80e9034667a9e30d1e82bc528e
Source dataset
uspto-grants-1988_03
Patent number
US04730008

Reaction notes

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