Water → 5-Hydroxy-4-(4-methoxy-phenyl)-5H-furan-2-one

HRID 2042554Notes

Reaction equation

HRID 2042554 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.Cl.N1CCOCC1.O.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]=[O:25])=[CH:19][CH:18]=1>O1CCOCC1>[OH:25][CH:24]1[O:6][C:2](=[O:5])[CH:3]=[C:23]1[C:20]1[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 797824-MethoxyphenylacetaldehydeHCID 197884Morpholine, hydrochloride (1:1)HCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 596519785-Hydroxy-4-(4-methoxy-phenyl)-5H-furan-2-oneYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of glyoxalic acid hydrate (2.45 g, 26.6 mmol) and morpholine hydrochloride (3.28 g, 26.35 mmol) in dioxane (25 mL) was stirred as water (2 mL) was added. The homogeneous solution and 4-methoxyphenyl acetaldehyde (3.8 g, 25.3 mmol) was then added and the solution was stirred at reflux for 24 h. The solvent was evaporated and a solid was formed after addition of 20 mL of water. The solid was collected and washed with water to give 5.1 g (98%) of the product: MS m/z 189 (M−17+H).

Workup

  1. additionwas added
  2. temperatureat reflux for 24 h
  3. customThe solvent was evaporated
  4. customa solid was formed
  5. customThe solid was collected
  6. washwashed with water

Sources & evidence

ORD record
ord-89dae74cf104495fb0481110f7a9c10b
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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