Oxalic Acid → 3-Fluoro-2-methylphenol

HRID 855158Notes

Reaction equation

HRID 855158 reaction equation
[F:1][C:2]1[C:3]([CH3:15])=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5]C1CCCCO1.C(O)(=O)C(O)=O>CO>[F:1][C:2]1[C:3]([CH3:15])=[C:4]([OH:5])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 58934897HCID 58934897, compound

Product 1

HCID 3026283-Fluoro-2-methylphenolYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The 5.0 g (23.78 mmol) of 2-(3-fluoro-2-methylphenoxy)tetrahydro-2H-pyran was dissolved in 120 mL of methanol followed by addition of 3.21 g (35.67 mmol) of oxalic acid. The mixture was heat to 60° C. for 2 hours. The volatiles were removed in vacuo while maintaining a bath temperature of <29° C. to afford an oil, which was purified by silica gel chromatography with EtOAc/hexane (1:9). Concentration of the desired fractions afforded 2.19 g (73%) of a pale yellow oil, which later solidified upon standing: 1H NMR(CDCl3/400 MHz) 2.16 (d, 3H, J=2.0 Hz), 5.17 (s, 1H), 6.57 (d, 1H, J=8.4 Hz), 6.64 (t, 1H, J=8.8 hz), 7.00 (dd, 1H, J=8.4, 14.8 Hz); HRMS (EI+) m/z calcd for (C7H7FO) 126.0481, found 126.0470.

Workup

  1. customThe volatiles were removed in vacuo
  2. temperaturewhile maintaining a bath temperature of <29° C.
  3. customto afford an oil, which
  4. customwas purified by silica gel chromatography with EtOAc/hexane (1:9)

Sources & evidence

ORD record
ord-d4f731f77cef468f8660d703d3dc9445
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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