2-Methyl-6-phenyl-hexa-3,5-diyn-2-ol → Buta-1,3-diynylbenzene

HRID 1446051Notes

Reaction equation

HRID 1446051 reaction equation
CC(O)([C:4]#[C:5][C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C>C1(C)C=CC=CC=1>[C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)#[C:6][C:5]#[CH:4]

Participants

3

Reactant 1

HCID 40884452-Methyl-6-phenyl-hexa-3,5-diyn-2-ol

Product 1

HCID 11355482Buta-1,3-diynylbenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-methyl-6-phenyl-hexa-3,5-diyn-2-ol (3.8 g, 20.6 mmol) sodium hydride (60%, 83 mg, 2.06 mmol) and toluene (20 ml) was stirred at reflux for 1 hour. The mixture was evaporated. Chromatography on silica gel with petroleum and ethyl acetate (3:1), gave the title compound. Yield 0.54 g (21%).

Workup

  1. temperatureat reflux for 1 hour
  2. customThe mixture was evaporated

Sources & evidence

ORD record
ord-46b49c79abd846b4a293276004096a17
Source dataset
uspto-grants-2010_02
Patent number
US07667040B2

Reaction notes

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