Hydrochloric Acid → 2-Chloro-6-hydroxybenzaldehyde

HRID 1471669Notes

Reaction equation

HRID 1471669 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8](F)[C:5]=1[CH:6]=[O:7].Cl>CS(C)=O.O>[Cl:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:1])[C:5]=1[CH:6]=[O:7]

Participants

6

Reactant 3

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

Product 1

HCID 5283932-Chloro-6-hydroxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (10 g) was added slowly to a stirred solution of 2-chloro-6-fluoro-benzaldehyde (14.0 g, 88.3 mmol) in dimethylsulfoxide (20 mL) at 0° C., the reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was diluted with water (100 mL) and acidified to pH 2 with concentrated HCl. The precipitates were filtered, washed with water (2×100 mL) and dried over anhydrous sodium sulfate, to give a residue which was used directly in the next step. Yield: 8.5 g (62%). 1H NMR (400 MHz, CDCl3) δ ppm 6.85-7.02 (m, 2H) 7.39-7.47 (m, 1H) 10.41 (s, 1H) 11.95 (s, 1H).

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water (2×100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customto give a residue which

Sources & evidence

ORD record
ord-963fabdb29cc4bda942fa3bfe187c89e
Source dataset
uspto-grants-2015_04
Patent number
US09012457B2

Reaction notes

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