Water → 1-Ethynyl-3,5-dimethylbenzene
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]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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
- customthe reaction was then removed from ice/water bath
- customapproximately half of the organic solvent was removed in vacuo
- additionHexanes (1 L) and water (400 mL) were added
- washThe organic layer was washed with saturated brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f2b51390df4e4b91ab52cc34b220a5d7
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310247B1
Reaction notes
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