2,3-Dichlorobenzaldehyde → HCID 54186754, compound

HRID 620952Notes

Reaction equation

HRID 620952 reaction equation
C[O-].[Na+].[Cl-].[CH3:5][O:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl:27][C:28]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:29]=1[CH:30]=O>C(O)C>[CH3:5][O:6][CH:7]=[CH:30][C:29]1[CH:32]=[CH:33][CH:34]=[C:35]([Cl:36])[C:28]=1[Cl:27]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 54186754HCID 54186754, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

47.3 g of sodium methylate are introduced into 1.5 liters of absolute ethanol. There are then added portionwise, at room temperature, firstly 300.0 g of methoxymethyltriphenylphosphonium chloride and afterwards 142.5 g of 2,3-dichlorobenzaldehyde, and the reaction mixture is heated at 70° C. for about 60 hours. After cooling to room temperature, the mixture is filtered, and the filtrate is concentrated in vacuo. The residue is taken up in pentane, washed, again concentrated by evaporation, and filtered over SiO2 with dichloromethane. Excess solvent is removed in vacuo. There is thus obtained β-methoxy-2,3-dichlorostyrene as a 1:1 (E/Z) mixture in the form of a light-yellow oil.

Workup

  1. additionThere are then added portionwise, at room temperature
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated in vacuo
  4. washwashed
  5. concentrationagain concentrated by evaporation
  6. filtrationfiltered over SiO2 with dichloromethane
  7. customExcess solvent is removed in vacuo

Sources & evidence

ORD record
ord-8224d9011c62414fa19ee00f6a8630e4
Source dataset
uspto-grants-1989_04
Patent number
US04822919

Reaction notes

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