Water → 1-Ethynyl-4-propylbenzene

HRID 1707884Notes

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

Conditions

Temperature: 60 °C

Procedure

3-Methyl-1-(4'-propylphenyl)-1-butyne-3-ol (33 g) was dissolved in toluene (320 ml) under nitrogen atmosphere, and then sodium hydride (60% in 2 g of paraffin liquid) was added thereto. The mixture was stirred at 60° C. for 6 hours. The reaction solution was poured into water (300 ml), and then 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. 60° to 63° C./4 mmHg) to give 4-propylphenylacetylene (16 g).

Workup

extractionextracted with chloroform
washby washing with water three times
distillationAfter distilling off toluene and chloroform
distillationthe resultant was distilled under reduced pressure (b.p. 60° to 63° C./4 mmHg)

Sources & evidence

ORD record: ord-4f1873e3c3e44c4e993fac6958c7e019
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05356558

Reaction notes

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