Water → 1-Ethynyl-4-propylbenzene

HRID 1755620Notes

Reaction equation

HRID 1755620 reaction equation
CC(O)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[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][CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 152397712-Methyl-4-(4-propylphenyl)-3-butyn-2-ol

Product 1

HCID 27751331-Ethynyl-4-propylbenzeneYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

33 g of 3-methyl-1-(4'-propylphenyl)-1-butyn-3-ol was dissolved in 320 ml of toluene in nitrogen atmosphere, and 2 g of sodium hydride (60% in paraffin liquid) was added thereto. This was stirred for 6 hours at 60° C. The reaction solution was poured into 300 ml of water, extracted with chloroform and washed three times with water. Toluene and chloroform were removed by distillation, and the residue was distilled under reduced pressure (b.p. 60° to 63° C./4 mmHg) to obtain 16 g of 4-propylphenylacetylene.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. washwashed three times with water
  4. customToluene and chloroform were removed by distillation
  5. distillationthe residue was distilled under reduced pressure (b.p. 60° to 63° C./4 mmHg)

Sources & evidence

ORD record
ord-0999ccb38b794a64af17eba142998c6c
Source dataset
uspto-grants-1995_08
Patent number
US05437815

Reaction notes

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