Water → 5-Chloro-2,3-dihydroxybenzaldehyde

HRID 749432Notes

Reaction equation

HRID 749432 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:11]C)[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].O>Br>[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 962WaterHCID 51510865-Chloro-2-hydroxy-3-methoxybenzaldehyde

Product 1

HCID 219248625-Chloro-2,3-dihydroxybenzaldehydeYield 32.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

5-Chloro-2-hydroxy-3-methoxy-benzaldehyde (see J. Org. Chem. 56; 1991; 5451; 20.0 g, 107 mmol) was suspended in hydrobromic acid (100 mL of 47% in water). The mixture was refluxed for 6 h and then cooled to room temperature before dilution with water (300 mL). The formed precipitate was collected by filtration and then washed with water. After air drying, the solid material was purified by soaking with CH2Cl2 (4×150 mL). There was obtained 6.0 g (32%) of 5-chloro-2,3-dihydroxybenzaldehyde as a solid. 1H NMR (300 MHz, CDCl3): 5.7 (s, 1H), 7.1 (d, 1H), 7.2 (d, 1H), 9.8 (s, 1H), 11.0 (s, 1H).

Workup

  1. temperatureThe mixture was refluxed for 6 h
  2. filtrationThe formed precipitate was collected by filtration
  3. washwashed with water
  4. customAfter air drying
  5. customthe solid material was purified

Sources & evidence

ORD record
ord-06596c0af36c409eb8256a89b15ca4b6
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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