Hydrochloric Acid → 3-Chloro-4-methoxysalicylaldehyde

HRID 629379Notes

Reaction equation

HRID 629379 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:10].[Cl-].[Mg+2].[Cl-].[CH2:14]=[O:15].Cl>ClCCCl.C(N(CC)CC)C>[Cl:1][C:2]1[C:3]([OH:10])=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[CH:14]=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5360315Magnesium ChlorideHCID 155814712-Chloro-3-methoxyphenol

Product 1

HCID 133437063-Chloro-4-methoxysalicylaldehydeYield 94.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-chloro-3-methoxyphenol (19.3 g) in 1,2-dichloroethane (150 mL) were added triethylamine (73.7 g), magnesium chloride (57.8 g) and paraformaldehyde (36.5 g), and the mixture was stirred at 70° C. for 4 hr under nitrogen atmosphere. The reaction mixture was poured into 1N hydrochloric acid, and the precipitate was removed by filtration, and washed with dichloromethane. The organic layer was washed with 1N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (21.5 g).

Workup

  1. customthe precipitate was removed by filtration
  2. washwashed with dichloromethane
  3. washThe organic layer was washed with 1N hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b81d52eba97246f68e370c353edec73b
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

Loading…