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

HRID 750952Notes

Reaction equation

HRID 750952 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-49c9b6a31d874978876182aaba7e28a3
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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