Hexamethylenetetramine → 2-Fluoro-3-hydroxy-4-methoxybenzaldehyde

HRID 1057829Notes

Reaction equation

HRID 1057829 reaction equation
C1N2CN3CN(C2)CN1C3.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=1[OH:20].FC(F)(F)[C:23](O)=[O:24]>>[F:11][C:12]1[C:13]([OH:20])=[C:14]([O:18][CH3:19])[CH:15]=[CH:16][C:17]=1[CH:23]=[O:24]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acid2×HCID 27373672-Fluoro-6-methoxyphenol

Product 1

HCID 5981562-Fluoro-3-hydroxy-4-methoxybenzaldehydeYield 65%

Procedure

To a heated solution (80° C.) of hexamethylenetetramine (2.8 g, 20 mmol) in trifluoroacetic acid (10 mL) was added dropwise over a 50 minutes period 2-fluoro-6-methoxyphenol (1.42 g, 10 mmol) in trifluoroacetic acid (10 mL). The mixture was heated for an additional 1 hour, concentrated and water (50 ml) was added. The solution was stirred for 10 minutes and solid potassium carbonate was added until the solution was neutral. The solid that formed was collected to afford 1.1 g of 2-fluoro-3-hydroxy-4-methoxybenzaldehyde (65%). 1H NMR (500 MHz; DMSO-d6): δ3.90 (s, 3H); 6.98 (d, J=8.5 Hz, 1H); 7.31 (t, J=8.5 Hz, 1H); 9.66 (br, 1H); 10.02 (s, 1H).

Workup

  1. temperatureThe mixture was heated for an additional 1 hour
  2. concentrationconcentrated
  3. additionwater (50 ml) was added
  4. additionsolid potassium carbonate was added until the solution
  5. customThe solid that formed
  6. customwas collected

Sources & evidence

ORD record
ord-23ba6df2f22a4ca28ee3b95abb405764
Source dataset
uspto-grants-2003_02
Patent number
US06515003B1

Reaction notes

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