Diethyl Ether → Chloroisovaniline

HRID 486373Notes

Reaction equation

HRID 486373 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.C(O[Cl:17])(C)(C)C.CCOCC>CC(O)=O>[Cl:17][C:4]1[C:5]([OH:6])=[C:7]([O:8][CH3:9])[CH:10]=[CH:11][C:3]=1[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12127IsovanillinHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 603956ChloroisovanilineYield 69.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

41.2 g (0.271 mol) of isovanillin was dissolved in 160 ml of 90% AcOH under heating. 29.41 g of t-BuOCl was added dropwise to the solution while it was kept at 35° to 40° C. The solution was stirred at room temperature for 3 hours and then 200 ml of ether was added thereto. The mixture was left to stand overnight and crystals thus formed were separated by filtration and washed with ether. 42.0 g of the crude crystals were recrystallized from acetonitrile to obtain 35 g of 2-chloro-3-hydroxy-4-methoxybenzaldehyde (69%).

Workup

  1. temperatureunder heating
  2. customwas kept at 35° to 40° C
  3. waitThe mixture was left
  4. waitto stand overnight
  5. customcrystals thus formed
  6. customwere separated by filtration
  7. washwashed with ether
  8. custom42.0 g of the crude crystals were recrystallized from acetonitrile

Sources & evidence

ORD record
ord-340794740b714766947331040402f084
Source dataset
uspto-grants-1994_03
Patent number
US05292521

Reaction notes

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