Water → 1-Ethynyl-4-propylbenzene

HRID 1034103Notes

Reaction equation

HRID 1034103 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[C:9](Br)Br)=[CH:6][CH:5]=1)[CH2:2][CH3:3].CCCCCC.C([Li])CCC.O>O1CCCC1>[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]#[CH:9])=[CH:12][CH:13]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 152407014-Propyl-beta,beta-dibromostyreneHCID 178418244HCID 178418244, compound

Product 1

HCID 27751331-Ethynyl-4-propylbenzeneYield 27.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under nitrogen flow, the 27 g of 4-propyl-β,β-dibromostyrene was dissolved in 44 ml of tetrahydrofuran and cooled to -78° C. Two hundred ml of a butyl lithium hexane solution (1.6 mol/1 was added dropwise therein over a period of one hour. The solution was then agitated at room temperature for one and a half hours. After completion of the reaction, 200 ml of water was added. The crystals then were extracted with chloroform and washed three times with water. The remaining chloroform was distilled off, after which vacuum distillation (70° to 75° C./20 mmHg) was carried out to obtain 3.5 g of 4-propylphenylacetylene.

Workup

  1. additionwas added
  2. extractionThe crystals then were extracted with chloroform
  3. washwashed three times with water
  4. distillationThe remaining chloroform was distilled off
  5. distillationafter which vacuum distillation (70° to 75° C./20 mmHg)

Sources & evidence

ORD record
ord-a680a93fed5745528c0b7e354306abc6
Source dataset
uspto-grants-1994_05
Patent number
US05314640

Reaction notes

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