Formaldehyde → 2-BENZYL-PROPENAL

HRID 1384787Notes

Reaction equation

HRID 1384787 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:13](O)(=O)CCCCCCCCCCCCCCCCC.C(NCCCC)CCC>O>[CH2:7]([C:8](=[CH2:13])[CH:9]=[O:10])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5281Stearic AcidHCID 7707BenzenepropanalHCID 8148Dibutylamine

Product 1

HCID 109097042-BENZYL-PROPENALYield 3,762.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A four-necked 500-ml flask equipped with a thermometer and condenser was charged with 134 g (1.0 mol) of 3-phenylpropionaldehyde, 85 g (1.05 mol) of a 37% aqueous formalin solution and 6 g (0.02 mol) of stearic acid, followed by the dropwise addition of 9 g (0.07 mol) of dibutylamine at room temperature under a nitrogen atmosphere over 10 minutes. After the temperature was increased to 90° C., stirring was conducted at the same temperature for 30 minutes. After cooling, 200 ml of water were added to the reaction mixture. The resulting mixture was then extracted with 200 ml of hexane, followed by washing with 200 ml of water. The organic layer was dried and concentrated, whereby 161 g of a crude product were obtained. The crude product was distilled (3.5 mmHg, 80° C.), whereby 110 g (yield: 75%) of 2-benzylacrylaldehyde were obtained.

Workup

  1. customA four-necked 500-ml flask equipped with a thermometer and condenser
  2. temperatureAfter cooling
  3. extractionThe resulting mixture was then extracted with 200 ml of hexane
  4. washby washing with 200 ml of water
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customwhereby 161 g of a crude product were obtained
  8. distillationThe crude product was distilled (3.5 mmHg, 80° C.)

Sources & evidence

ORD record
ord-b09721c1a60e4d97924a1d0e781ef7f0
Source dataset
uspto-grants-2001_07
Patent number
US06262014B1

Reaction notes

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