Ethylene carbonate → 5-Ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-benzaldehyde

HRID 1266699Notes

Reaction equation

HRID 1266699 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([OH:13])=[CH:6][C:7]([F:12])=[C:8]([CH:11]=1)[CH:9]=[O:10])[CH3:2].C1(=O)O[CH2:17][CH2:16][O:15]1>C1(C)C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:3][C:4]1[C:5]([O:13][CH2:17][CH2:16][OH:15])=[CH:6][C:7]([F:12])=[C:8]([CH:11]=1)[CH:9]=[O:10])[CH3:2]

Participants

5

Reactant 2

HCID 7303Ethylene carbonateHCID 226475845-Ethoxy-2-fluoro-4-hydroxy-benzaldehyde

Product 1

HCID 219055785-Ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-benzaldehydeYield 90.8%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

The 5-ethoxy-2-fluoro-4-hydroxy-benzaldehyde (9.15 g) described in example 1.3 was dissolved in toluene (80 ml). Ethylene carbonate (5.25 g) and tetrabutylammonium iodide (1.83 g) were added and the mixture was heated to reflux for 22 h. The mixture was cooled to room temperature and filtered over a plug of silica gel. The product was eluted with hexane/ethyl acetate. The solvent was evaporated and the solid was washed with hot hexane to give 10.3 g of 5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-benzaldehyde as a slightly orange solid. MS: 228 ([M]+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 22 h
  3. filtrationfiltered over a plug of silica gel
  4. washThe product was eluted with hexane/ethyl acetate
  5. customThe solvent was evaporated
  6. washthe solid was washed with hot hexane

Sources & evidence

ORD record
ord-f731d73c87cb4ed4aedeea270298d89c
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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