Ethylene Glycol → 2-(2-Fluoro-4-methoxyphenyl)-1,3-dioxolane

HRID 2212588Notes

Reaction equation

HRID 2212588 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:12](O)[CH2:13][OH:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]1[O:14][CH2:13][CH2:12][O:5]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 27348732-Fluoro-4-methoxybenzaldehyde

Product 1

HCID 219664732-(2-Fluoro-4-methoxyphenyl)-1,3-dioxolaneYield 51.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-fluoro-4-methoxy-benzaldehyde (13.98 g, 90.7 mmol) in toluene (100 mL) was added ethylene glycol (101 mL, 1.81 mol) and p-toluenesulfonic acid monohydrate (1.04 g, 5.44 mmol). The reaction mixture was heated at reflux for 16 hrs. The water was removed using a Dean Starck apparatus. After cooling, aqueous potassium carbonate (10%, 200 mL) was added and the mixture stirred for 30 minutes. The solution was extracted with ethyl acetate. The organic phase was washed successively with 10% aqueous potassium carbonate, brine and dried (MgSO4). The residue was purified on silica gel (eluent: 10% ethyl acetate in hexane) to give 9.187 g of 2-(2-fluoro-4-methoxy-phenyl)-[1,3] dioxolane (51%). 1H NMR (300 MHz; CDCl3): 3.81 (s, 3 H), 4.06 (m, 2 H), 4.15 (m, 2 H), 6.03 (s, 1 H), 6.60 (dd, J=12.3 and 2.7 Hz, 1 H), 6.72 (d, J=8.4 Hz, 1 H), 7.44 (t, J=8.4 Hz, 1 H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 hrs
  3. customThe water was removed
  4. temperatureAfter cooling
  5. additionaqueous potassium carbonate (10%, 200 mL) was added
  6. extractionThe solution was extracted with ethyl acetate
  7. washThe organic phase was washed successively with 10% aqueous potassium carbonate, brine
  8. dry with materialdried (MgSO4)
  9. customThe residue was purified on silica gel (eluent: 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6349dc9a5451446f9c055eca2b74d36d
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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