Ethanol → HCID 21474299, compound

HRID 2294243Notes

Reaction equation

HRID 2294243 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][CH:3]=1.[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.C(O)C>O.[OH-].[Na+]>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]([OH:15])[C:3]2[O:4][CH:5]=[CH:6][C:7](=[O:8])[C:2]=2[OH:1])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 680234-FluorobenzaldehydeHCID 681293-Hydroxy-4H-pyran-4-one2×

Product 1

HCID 21474299HCID 21474299, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-[4-Fluorophenyl)-hydroxy-methyl]-3-hydroxy-pyran-4-one: With stirring at room temperature, 5.6 g of pyromeconic acid (3-hydroxy-pyran-4-one) [CAS No.: 496-63-9] are dissolved in 10 ml of water and 24.5 ml of 2N NaOH. 6.33 g of 4-fluorobenzaldehyde and 25 ml of ethanol are added and the reaction mixture is stirred at room temperature for 18 hours. For working-up, the ethanol is removed using a rotary evaporator and the aqueous solution that remains is neutralised with 24.5 ml of 2N HCl. The product that has crystallised out is filtered off, washed with water and dried, yielding 2-[(4-fluorophenyl)-hydroxy-methyl]-3-hydroxy-pyran-4-one in the form of colourless crystals. M.p.: 154°-156° C.

Workup

  1. customthe ethanol is removed
  2. customa rotary evaporator
  3. customThe product that has crystallised out
  4. filtrationis filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-64518113ca304c509dae0d0d8c33733e
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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