2-Acetamidobenzyl alcohol → N-(2-formylphenyl)acetamide

HRID 971307Notes

Reaction equation

HRID 971307 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][OH:8])(=[O:3])[CH3:2]>C(Cl)(Cl)Cl.O=[Mn]=O>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 3392922-Acetamidobenzyl alcohol

Product 1

HCID 326664N-(2-formylphenyl)acetamideYield 73%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of N-acetyl-2-amino-benzylalcohol (20 g) in dry CHCl3 (500 mL) was added MnO2 (160 g, 8 equivalents) and allowed to stir at room temperature for 12 h. The reaction mixture was filtered through celite and concentrated. The crude product was recrystallised from CHCl3/petrol ether to give N-acetyl-2-aminobenzaldehyde (14 g, 73%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated
  3. customThe crude product was recrystallised from CHCl3/petrol ether

Sources & evidence

ORD record
ord-6b72ab55819f44d887a00194ca641705
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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