Sodium Chloride → HCID 54461779, compound

HRID 1359544Notes

Reaction equation

HRID 1359544 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH3:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.[Cl-].[Na+]>C(OCC)C>[CH3:2][O:3][CH:4]=[CH:34][C:33]1[CH:36]=[CH:37][C:30]([CH3:29])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 77254-MethylbenzaldehydeHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 178418339Butyllithium

Product 1

HCID 54461779HCID 54461779, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

28.5 g of methoxymethyltriphenylphosphonium chloride is introduced into 350 ml of diethyl ether under nitrogen. At 0° C., 39.95 ml of n-butyllithium solution (1.6 M in hexane) is added in drops, and it is stirred for one hour at room temperature. 10 g of 4-methylbenzaldehyde in 50 ml of diethyl ether is now added, and it is stirred for one more hour. Sodium chloride solution is added to the reaction mixture, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. After chromatography on silica gel with ethyl acetate/hexane, 7.8 g of 1-methoxy-2-(4-methylphenyl)-ethene 36 (E,Z-mixture) is obtained as a colorless oil, which is dissolved in 200 ml of acetone and is stirred overnight under nitrogen with 10 ml of 2N hydrochloric acid. Sodium chloride solution is added, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. Chromatographic purification on silica gel with ethyl acetate/hexane yields 4.5 g of title compound 37 as a colorless oil.

Workup

  1. stirringit is stirred for one more hour
  2. extractionextracted with ethyl acetate
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-52e09485c7b744f797ce5583663ee964
Source dataset
uspto-grants-2003_07
Patent number
US06600058B1

Reaction notes

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