p-Toluenesulfonic acid monohydrate → 2,2-Diethoxy-1-(4-fluorophenyl)ethanone

HRID 500103Notes

Reaction equation

HRID 500103 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([OH:11])[OH:10])=[CH:4][CH:3]=1.C([O-])([O-])O[CH2:15][CH3:16].O.[C:20]1(C)C=CC(S(O)(=O)=O)=C[CH:21]=1>ClCCl>[CH2:20]([O:11][CH:9]([O:10][CH2:15][CH3:16])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:12])[CH3:21]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 112752531-(4-Fluorophenyl)-2,2-dihydroxyethanoneHCID 53630039Ethylorthoformate

Product 1

HCID 224161332,2-Diethoxy-1-(4-fluorophenyl)ethanoneYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-2,2-dihydroxyethanone (4.0 g, 0.024 mol), ethyl orthoformate (7.3 g, 49 mmol), and p-toluenesulfonic acid monohydrate (200 g, 1.05 mol) in dichloromethane (50 mL) was refluxed for 40 min. After cooling to room temperature (RT), the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with dichloromethane to give the desired product (5.2 g). 1H-NMR (300 MHz, CDCl3): 8.18-8.25 (m, 2H), 7.08-7.16 (m, 2H), 5.18 (s, 1H), 3.58-3.82 (m, 4H), 1.25 (t, J=7.0 Hz, 6H).

Workup

  1. temperaturewas refluxed for 40 min
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-e511de98643b4ed98cb334a3dc7b4904
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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