Bromide ion → 1-(2-Methoxyethenyl)-4-(1-methylbutyloxy)benzene

HRID 21887Notes

Reaction equation

HRID 21887 reaction equation
C([Li])CCC.[Br-].[CH3:7][CH:8]([O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)[CH2:9][CH2:10][CH3:11].[O:21]1[CH2:25]CC[CH2:22]1>CCCCCC>[CH3:22][O:21][CH:25]=[CH:17][C:16]1[CH:19]=[CH:20][C:13]([O:12][CH:8]([CH3:7])[CH2:9][CH2:10][CH3:11])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 8028Tetrahydrofuran2×HCID 199306244-(1-Methylbutyloxy)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 537267651-(2-Methoxyethenyl)-4-(1-methylbutyloxy)benzene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution containing butyllithium dissolved in hexane was added to a solution containing 120 g of methoxymethyltriphenylphosphoni bromide dissolved in tetrahydrofuran (THF), in an atmosphere of argon, and the mixture was stirred for one hour at room temperature. A solution of the compound (30) dissolved in THF was added thereto and stirring was continued for two hours. The reaction solution was washed with water, was dried over magnesium sulfate, and was then concentrated. The residue was purified by column chromatography to obtain 1-(2-methoxyethenyl)-4-(1-methylbutyloxy)benzene (31).

Workup

  1. additionwas added to a solution
  2. additionwas added
  3. stirringstirring
  4. waitwas continued for two hours
  5. washThe reaction solution was washed with water
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationwas then concentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c98de13488664eb499e8466680457ad6
Source dataset
uspto-grants-1995_06
Patent number
US05425897

Reaction notes

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