Hydrochloric Acid → 2-Chloro-6-hydroxybenzaldehyde

HRID 1712914Notes

Reaction equation

HRID 1712914 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:3]=1[CH:4]=[O:5].[OH-:11].[K+].Cl>CS(C)=O.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 678472-Chloro-6-fluorobenzaldehyde

Product 1

HCID 5283932-Chloro-6-hydroxybenzaldehydeYield 61.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-chloro-6-fluorobenzaldehyde (2.44 g, 15.4 mmol) in DMSO (20 mL) at 0° C. was added potassium hydroxide (2.23 g, 33.8 mmol) slowly. The reaction mixture was allowed to stir and warm to rt overnight and then diluted with water (65 mL). The mixture was acidified to pH<1 with conc. HCl. A white solid formed and was filtered, washed with water, and dried to give 2-chloro-6-hydroxybenzaldehyde (1.48 g, 61%). LCMS: (FA) ES-155.0.

Workup

  1. customA white solid formed
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-084b7c4228bd4689aea36a6a7fd7ff0c
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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