Water → 1-Ethynyl-4-pentylbenzene

HRID 1707887Notes

Reaction equation

HRID 1707887 reaction equation
CC(O)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[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][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 189600502-Methyl-4-(4-pentylphenyl)-3-butyn-2-ol

Product 1

HCID 27751311-Ethynyl-4-pentylbenzeneYield 78.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

3-Methyl-1-(4'-pentylphenyl)-1-butyne-3-ol (82 g) was dissolved in toluene (900 ml) under nitrogen atmosphere, and then sodium hydride (60% in paraffin liquid; 5.6 g) was added thereto, followed by stirring at 60° C. for 6 hours. The reaction solution was poured into water (500 ml), and extracted with chloroform, followed by washing with water three times. After distilling off toluene and chloroform, the resultant was distilled under reduced pressure (b.p. 85° to 90° C./3 mmHg) to give 4-pentylphenylacetylene (48 g).

Workup

  1. extractionextracted with chloroform
  2. washby washing with water three times
  3. distillationAfter distilling off toluene and chloroform
  4. distillationthe resultant was distilled under reduced pressure (b.p. 85° to 90° C./3 mmHg)

Sources & evidence

ORD record
ord-38f07c5ccb884bc3b6fdd552c381312b
Source dataset
uspto-grants-1994_10
Patent number
US05356558

Reaction notes

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