Hydrochloric Acid → 3,5-Difluoro-4-hydroxybenzaldehyde

HRID 2425767Notes

Reaction equation

HRID 2425767 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].[CH2:10]1N2CN3CN(C2)CN1C3.Cl.[OH-:21].[Na+]>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([F:8])[C:3]=1[OH:9])[CH:10]=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 14798Sodium HydroxideHCID 943922,6-Difluorophenol

Product 1

HCID 101925843,5-Difluoro-4-hydroxybenzaldehydeYield 99%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2,6-difluorophenol (5.00 g, 38.43 mmol) and hexamethylenetetramine (HMTA) (5.93 g, 42.30 mmol) in trifluoroacetic acid (TFA) (50 ml) was heated under reflux 16 h. The reaction mixture was cooled to room temperature, poured on to HCl (150 ml 4 M) and stirred for 3 hours and brought to pH 3 via the addition of NaOH solution (5 M). The organic phase was extracted in to diethyl ether (4×100 ml), the combined ethereal extracts dried (MgSO4) and the solvent removed in vacuo. The residue were purified by column chromatography [silica gel, eluted with hexane:EtOAc, 4:1] providing white solid (6.1 g, 38 mmol, 99%).

Workup

  1. temperatureunder reflux 16 h
  2. extractionThe organic phase was extracted in to diethyl ether (4×100 ml)
  3. dry with materialthe combined ethereal extracts dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue were purified by column chromatography [silica gel, eluted with hexane:EtOAc, 4:1]

Sources & evidence

ORD record
ord-67104766cb9e451ea4c1799cc1ad9295
Source dataset
uspto-grants-2011_06
Patent number
US07964878B2

Reaction notes

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