Sodium Hydroxide → 1-Hex-5-ynyl-4-methoxy-benzene

HRID 1768050Notes

Reaction equation

HRID 1768050 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[C:14][Si](C)(C)C)=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[CH2:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH2:10][CH2:11][CH2:12][C:13]#[CH:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23614554[6-(4-Methoxy-phenyl)-hex-1-ynyl]-trimethyl-silane

Product 1

HCID 236145351-Hex-5-ynyl-4-methoxy-benzeneYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.20 g (12.3 mmol) [6-(4-methoxy-phenyl)-hex-1-ynyl]-trimethyl-silane, 50 ml methanol and 12.3 ml (24.6 mmol) 2N NaOH was stirred for 2 h at r.t. After neutralization with 13 ml 2N HCl methanol was distilled off and the aqueous phase extracted with diethyl ether. Drying (Na2SO4) and removal of solvents in vacuo gave 1.80 g (78%) of the title compound.

Workup

  1. distillationAfter neutralization with 13 ml 2N HCl methanol was distilled off
  2. extractionthe aqueous phase extracted with diethyl ether
  3. customDrying
  4. custom(Na2SO4) and removal of solvents in vacuo

Sources & evidence

ORD record
ord-7c14c2a2fccd4c928dac8fcd26db4931
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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