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

HRID 1884482Notes

Reaction equation

HRID 1884482 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, 3 H); 6.98 (d, J=8.5 Hz, 1 H); 7.31 (t, J=8.5 Hz, 1 H); 9.66 (br, 1 H); 10.02 (s, 1 H).

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-4c69d5a8b10b4f78acca93620543b5d4
Source dataset
uspto-grants-2004_07
Patent number
US06765013B2

Reaction notes

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