Chloroacetyl chloride → 3-(Chloroacetylamino)-4-hydroxy-benzaldehyde

HRID 566873Notes

Reaction equation

HRID 566873 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13]CCCO2)=[CH:4][C:3]=1[N+:14]([O-])=O.[H][H].[Cl:19][CH2:20][C:21](Cl)=[O:22].C(=O)(O)[O-].[Na+]>[Ni].O1CCCC1>[Cl:19][CH2:20][C:21]([NH:14][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[OH:1])[CH:8]=[O:13])=[O:22]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 5972564-(1,3-Dioxan-2-yl)-2-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 212639083-(Chloroacetylamino)-4-hydroxy-benzaldehydeYield 65%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-[4-Hydroxy-3-nitro-phenyl]-1,3-dioxane (5.6 g, 24.9 mmol) is reduced in the presence of Raney nickel in 50 mL of tetrahydrofuran (THF) under a hydrogen atmosphere. When the theoretical amount of hydrogen is taken up, the catalyst is removed by filtration. Chloroacetyl chloride (2.5 g, 22.2 mmol) and sodium bicarbonate (3.6 g, 42.3 mmol) are added to the filtrate at room temperature and the mixture is stirred for 1 hour under argon. The solvent is evaporated and the remaining solid is taken up in 50 mL of methanol. The solution is acidified to a pH of about one with 1.0 N HCl and stirred at room temperature for 1 hour. The precipitate is collected and dried under vacuum to give 2.5 g (65% yield) of 3-(chloroacetylamino)-4-hydroxy-benzaldehyde as a hydrate; mp 190-192° C.

Workup

  1. customthe catalyst is removed by filtration
  2. customThe solvent is evaporated
  3. stirringstirred at room temperature for 1 hour
  4. customThe precipitate is collected
  5. customdried under vacuum

Sources & evidence

ORD record
ord-854deb46b3af4da6a7f58fc69e856cf4
Source dataset
uspto-grants-2001_01
Patent number
US06177422B1

Reaction notes

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