Hydrochloric Acid → 2-Chloro-4-hydroxybenzaldehyde

HRID 62890

Reaction equation

HRID 62890 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#N.CC(C[AlH]CC(C)C)C.Cl.C1C[O:24]CC1>>[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:24]

Participants

5

Conditions

Temperature
-78 °C

Procedure

After 2-chloro-4-hydroxy-benzonitrile (2 g, 0.013 mol) was dissolved in anhydrous THF (40 mL), DIBAL-H 1M hexane solution (21.7 mL, 0.032 mol) was added thereto at −78° C., and the mixture was stirred for 1 hour, and then stirred at room temperature for 2 hours. After the termination of the reaction, the reactant was added with 1M HCl at 0° C. and then extracted with EtOAc. The organic layer was separated, dried with MgSO4, and concentrated under reduced pressure to obtain the title compound, which was used in the next step without a separate purification process.

Workup

  1. stirringstirred at room temperature for 2 hours
  2. customAfter the termination of the reaction
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40264fe6f229486c8612a904a343b595
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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