2,3-Dichlorobenzaldehyde → HCID 54186754, compound

HRID 247100Notes

Reaction equation

HRID 247100 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-1fa3ec5ff9c348838d9b4648cf07a1b6
Source dataset
uspto-grants-1987_11
Patent number
US04705801

Reaction notes

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