3-Phenylprop-2-Enal → HCID 53774898, compound

HRID 1646058Notes

Reaction equation

HRID 1646058 reaction equation
C[O-].[Na+].[CH:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:14][C:15]1([CH3:25])[CH2:20][O:19][CH:18]([C:21](=[O:24])[CH2:22][CH3:23])[O:17][CH2:16]1>CO>[CH3:25][C:15]1([CH3:14])[CH2:16][O:17][CH:18]([C:21](=[O:24])[C:22]([CH3:23])=[CH:4][CH:5]=[CH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:19][CH2:20]1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 10942334Sodium MethoxideHCID 13051534HCID 13051534, compound

Product 1

HCID 53774898HCID 53774898, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
2.5 °C

Procedure

7.2 g of a 30% strength by weight solution of sodium methylate in methanol were added dropwise to a solution of 52.9 g of cinnamaldehyde and 68.9 g of 5,5-dimethyl-2-propionyl-1,3-dioxane in 200 ml of methanol in the course of 15 minutes at 0-5° C., and the mixture was stirred for a further 2 hours at 0-5° C. Thereafter, the reaction solution was seeded with a few crystals of the product and stirred overnight at room temperature. After the precipitate had been filtered off under suction and washed with cold methanol, 29.8 g of the product were obtained in the form of colorless crystals of melting point 122-125° C.

Workup

  1. stirringstirred overnight at room temperature
  2. filtrationAfter the precipitate had been filtered off under suction
  3. washwashed with cold methanol

Sources & evidence

ORD record
ord-ab11e39431894bc59138a47fb450a590
Source dataset
uspto-grants-1993_01
Patent number
US05177222

Reaction notes

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