4-Hydroxybenzaldehyde → 3-Chloro-4-hydroxybenzaldehyde

HRID 1841371Notes

Reaction equation

HRID 1841371 reaction equation
[Cl:1]Cl.[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1>C(O)(=O)C>[Cl:1][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=1[OH:3])[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 24526Chlorine2×

Product 1

HCID 170223-Chloro-4-hydroxybenzaldehydeYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Acetic acid (300 ml) was bubbled with chlorine gas to make 38.38 g (0.541 mol) of chlorine. 4-Hydroxybenzaldehyde (66.1 g, 0.541 mol) was dissolved in acetic acid (300 ml) and stirred, during which the acetic acid solution containing chlorine as prepared above was slowly added thereto over 2 hours. The resulting mixture was stirred for further 2 hours. After completion of reaction, the reaction solution was concentrated. To the residue was added water (1L), which was then filtered, washed with water (500 ml) and dried to give 63.16 g (0.403 mol, Yield 75%) of the title compound.

Workup

  1. customAcetic acid (300 ml) was bubbled with chlorine gas
  2. customas prepared
  3. additionabove was slowly added
  4. customAfter completion of reaction
  5. concentrationthe reaction solution was concentrated
  6. additionTo the residue was added water (1L), which
  7. filtrationwas then filtered
  8. washwashed with water (500 ml)
  9. customdried

Sources & evidence

ORD record
ord-602fa5edabc743669bf8992c69b815a9
Source dataset
uspto-grants-2004_01
Patent number
US06683095B2

Reaction notes

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