Water → Methyl 2,4-dichloro-3-formylbenzoate

HRID 1368821Notes

Reaction equation

HRID 1368821 reaction equation
C[N+]1([O-])CC[O:5]CC1.Br[CH2:10][C:11]1[C:12]([Cl:22])=[C:13]([CH:18]=[CH:19][C:20]=1[Cl:21])[C:14]([O:16][CH3:17])=[O:15].O>C(#N)C>[Cl:22][C:12]1[C:11]([CH:10]=[O:5])=[C:20]([Cl:21])[CH:19]=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 15477480Methyl 3-(bromomethyl)-2,4-dichlorobenzoate

Product 1

HCID 15430822Methyl 2,4-dichloro-3-formylbenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At reflux, 696.2 g (2.97 mol) of aqueous 50% strength N-methylmorpholine N-oxide solution were added to a solution of 312.0 g (0.99 mol) of methyl 3-bromomethyl-2,4-dichlorobenzoate in 2 l of acetonitrile. After stirring for 48 hours at room temperature, the reaction solution was stirred into 6 l of water. The precipitate was filtered off with suction, washed with water and dried under reduced pressure. 141.3 g of methyl 2,4-dichloro-3-formylbenzoate were obtained.

Workup

  1. temperatureAt reflux
  2. filtrationThe precipitate was filtered off with suction
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-36f4287fd63b4528ae342fde16774b78
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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