Water → 1-Ethynyl-3,5-dimethylbenzene

HRID 382900Notes

Reaction equation

HRID 382900 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[CH:6]=1.[OH-].[K+].O>C1COCC1.CO>[CH3:12][C:7]1[CH:6]=[C:5]([C:4]#[CH:3])[CH:10]=[C:9]([CH3:11])[CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 18362235(3,5-Dimethyl-phenylethynyl)-trimethyl-silane

Product 1

HCID 64326111-Ethynyl-3,5-dimethylbenzeneYield 82.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of crude 1-trimethylsilyl-2-(3,5-dimethylphenyl)acetylene (105 mmol, theoretical maximum) in THF (70 mL) and MeOH (280 mL) was cooled in an ice/water bath during addition of 8N KOH (16 mL, 128 mmol) and water (25 mL) and the reaction was then removed from ice/water bath. After 1 h, approximately half of the organic solvent was removed in vacuo. Hexanes (1 L) and water (400 mL) were added. The organic layer was washed with saturated brine, dried (Na2SO4), and concentrated to give 11.3 g of 1-(3,5-dimethylphenyl)acetylene as a brown oil:

Workup

  1. customthe reaction was then removed from ice/water bath
  2. customapproximately half of the organic solvent was removed in vacuo
  3. additionHexanes (1 L) and water (400 mL) were added
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f2b51390df4e4b91ab52cc34b220a5d7
Source dataset
uspto-grants-2001_10
Patent number
US06310247B1

Reaction notes

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