Water → 1-Butyl-4-ethynylbenzene

HRID 1707896Notes

Reaction equation

HRID 1707896 reaction equation
CC(O)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1.[H-].[Na+].O>C1(C)C=CC=CC=1>[CH2:11]([C:8]1[CH:7]=[CH:6][C:5]([C:4]#[CH:3])=[CH:10][CH:9]=1)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 189599944-(4-Butylphenyl)-2-methyl-3-butyn-2-ol

Product 1

HCID 27751321-Butyl-4-ethynylbenzeneYield 86.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

3-Methyl-1-(4'-butylphenyl)-1-butyne-3-ol (100 g) was dissolved in toluene (900 ml) under nitrogen atmosphere, and then sodium hydride (60% in paraffin liquid; 5.7 g) was added thereto, followed by stirring at 60° C. for 6 hours. The reaction solution was poured into water (500 ml), and then extracted with chloroform, followed by washing with water 3 times. After distilling off toluene and chloroform, the resultant was distilled under reduced pressure (b.p. 62° to 65° C./3 mmHg) to give 4-butylphenylacetylene (63 g).

Workup

  1. extractionextracted with chloroform
  2. washby washing with water 3 times
  3. distillationAfter distilling off toluene and chloroform
  4. distillationthe resultant was distilled under reduced pressure (b.p. 62° to 65° C./3 mmHg)

Sources & evidence

ORD record
ord-71064b572e43421d8cd72652a836ec98
Source dataset
uspto-grants-1994_10
Patent number
US05356558

Reaction notes

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