Water → 2,3-Dichloro-4-methoxybenzaldehyde

HRID 2058583Notes

Reaction equation

HRID 2058583 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CN(C)C=O>[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 5283802,3-Dichloro-4-hydroxybenzaldehyde

Product 1

HCID 130156892,3-Dichloro-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,3-dichloro-4-hydroxybenzaldehyde (19.1 gm., ;b 0.1 mole) and potassium carbonate (34.4 gm., 0.25 mole) in dimethylformamide (50 ml.) is stirred and treated dropwise over 15 minutes with dimethyl sulfate (14.1 gm., 0.11 mole). The reaction is exothermic; after 45 minutes the mixture is poured with stirring into water (300 ml.). The solid product that separates is removed by filtration, washed with water and then washed with a little methanol. After drying the yield of 2,3-dichloro-4-methoxybenzaldehyde is 16 gm., m.p., 117°-118° C.

Workup

  1. additionafter 45 minutes the mixture is poured
  2. customThe solid product that separates is removed by filtration
  3. washwashed with water
  4. washwashed with a little methanol
  5. dry with materialAfter drying the yield of 2,3-dichloro-4-methoxybenzaldehyde
  6. customm.p., 117°-118° C.

Sources & evidence

ORD record
ord-f05456d6c96d4d2a9db4fd6fc910d597
Source dataset
uspto-grants-1982_03
Patent number
US04317922

Reaction notes

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