Hydrochloric Acid → HCID 737218, compound

HRID 1197718Notes

Reaction equation

HRID 1197718 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[OH-].[Na+].[C:12]([OH:19])(=[O:18])[CH2:13][CH2:14][C:15]([CH3:17])=[O:16].Cl>CCO>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:17][C:15](=[O:16])[CH2:14][CH2:13][C:12]([OH:19])=[O:18])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 77254-MethylbenzaldehydeHCID 11579Levulinic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 737218HCID 737218, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Tolualdehyde (39.6 g, 0.33 mol) and 2M NaOH solution (230 ml) are added to a solution of levulinic acid (39.5 g, 0.34 mol) in EtOH (85 ml) over 1 hour. The resulting clear solution is poured into ice and acidified with 6M HCl. The resulting gum obtained is crystallised with acetone/water and recrystallised from CH2Cl2 to yield 14.0 g of 6-(4 methylphenyl)-4-oxo-hex-5-enoic acid as colourless crystals m.p. 129-130.

Workup

  1. additionThe resulting clear solution is poured into ice
  2. customThe resulting gum obtained
  3. customis crystallised with acetone/water
  4. customrecrystallised from CH2Cl2

Sources & evidence

ORD record
ord-45335385a0dd4380b8f11034fa4d7f59
Source dataset
uspto-grants-1994_01
Patent number
US05277709

Reaction notes

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