4-Hydroxybenzaldehyde → 3-Chloro-4-hydroxybenzaldehyde

HRID 1370121Notes

Reaction equation

HRID 1370121 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[OH:1])[CH:6]=[O:7]

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 31398Chlorosuccinimide

Product 1

HCID 170223-Chloro-4-hydroxybenzaldehydeYield 66.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-hydroxybenzaldehyde (100 g) in chloroform (1 L) was added N-chlorosuccinimide (120 g) at ambient temperature and the mixture was stirred at 50° C. for 18 hours. After evaporation of the solvent, the residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The crude crystals was washed with diisopropyl ether and recrystallized from a mixture of ethyl acetate and n-hexane to obtain 3-chloro-4-hydroxybenzaldehyde (85.8 g) as colorless crystals.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. washThe crude crystals was washed with diisopropyl ether
  7. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-1686a51d80934a25b5050ed27cf628cc
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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