Hydrochloric Acid → 3-Fluoro-4-hydroxybenzaldehyde

HRID 459158Notes

Reaction equation

HRID 459158 reaction equation
Cl.[O:2]1CCO[CH:3]1[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([F:14])[CH:8]=1>C1COCC1.O>[F:14][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[OH:13])[CH:3]=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 184436734-[1,3]Dioxolan-2-yl-2-fluorophenol

Product 1

HCID 5872503-Fluoro-4-hydroxybenzaldehydeYield 95.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1N HCl (1 mL) and 4-[1,3]dioxolan-2-yl-2-fluoro-phenol (250 mg, 1.35 mmol) in THF (2 mL) was stirred, at room temperature for 1 hour. The mixture was diluted with water and extracted with methylene chloride (4×10 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under vacuum. The residue was chromatographed (silica gel, hexanes/ethyl acetate 1:1) to produce 3-Fluoro-4-hydroxy-benzaldehyde as a white solid (180 mg, 95%). 1H-NMR (CDCl3, 200.15 MHz): 9.84 (d, 1H, J=2.4), 7.68–7.59 (m, 2H), 7.15 (t, 1H, J=8.5), 6.5 (sa, 1H).

Workup

  1. extractionextracted with methylene chloride (4×10 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was chromatographed (silica gel, hexanes/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-91e7f057624e4f06a19f010044a84fa2
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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