Methyl 4-Formylbenzoate → Methyl 4-(2-methoxyethenyl)benzoate

HRID 1769426

Reaction equation

HRID 1769426 reaction equation
C([Li])CCC.[Br-].[CH3:7][O:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:29]([C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=1)=O>CCCCCC.O1CCCC1>[CH3:7][O:8][CH:9]=[CH:29][C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 2773654(Methoxymethyl)triphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 54136641Methyl 4-(2-methoxyethenyl)benzoateYield 80.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In an atmosphere of argon, a solution containing butyllithium dissolved in hexane was added to a solution containing 120 g of methoxymethyltriphenylphosphonium bromide dissolved in tetrahydrofuran (THF), and the mixture was stirred for one hour at room temperature. A solution containing 50 g of methyl 4-formylbenzoate dissolved in THF was added thereto, and stirring was continued for two hours. The reaction solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to obtain 47 g of methyl 4-(2-methoxyethenyl)benzoate (45).

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 materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fd9f31cfc93d46bd8bad2836b65b2953
Source dataset
uspto-grants-1995_01
Patent number
US05380915

Linked notes

Loading…