Ethanol → HCID 57151975, compound

HRID 2399259Notes

Reaction equation

HRID 2399259 reaction equation
[CH3:1][C:2]([CH2:4][CH2:5][C:6]([OH:8])=[O:7])=[O:3].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[CH:14]=O.[CH2:23](O)[CH3:24]>O.[OH-].[Na+]>[O:3]=[C:2]([CH:1]=[CH:23][CH2:24][CH2:14][C:13]1[CH:12]=[C:11]([O:10][CH3:9])[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[CH:16]=1)[CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 702EthanolHCID 68583,4,5-TrimethoxybenzaldehydeHCID 11579Levulinic Acid

Product 1

HCID 57151975HCID 57151975, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of laevulinic acid (50 g, 0.43 mol) in water (200 ml) was added to a mixture of 3,4,5-trimethoxybenzaldehyde (85 g, 0.43 mol) in ethanol (150 ml) and sodium hydroxide solution (5%, 700 ml). The mixture was warmed with vigorous stirring until all the aldehyde had dissolved and was then poured onto ice (ca 2 Kg). It was then acidified to pH3-4 and left overnight. The crystalline material formed was filtered off, dried in vacuo and then recrystallised from ethanol to give pale yellow crystals (30.08 g), m.p. 187°-9°.

Workup

  1. temperatureThe mixture was warmed
  2. dissolutionhad dissolved
  3. additionwas then poured onto ice (ca 2 Kg)
  4. customThe crystalline material formed
  5. filtrationwas filtered off
  6. customdried in vacuo
  7. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-3d1702a213ec4a29a9772274e76be257
Source dataset
uspto-grants-1995_09
Patent number
US05447956

Reaction notes

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