Acetone → 1,5-bis[4-(2,3-epoxypropyloxy)phenyl]penta-1,4-dien-3-one

HRID 894101Notes

Reaction equation

HRID 894101 reaction equation
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][C:7]=1OC)[CH:2]1[O:4][CH2:3]1.[OH-:16].[Na+].[CH3:18][C:19]([CH3:21])=[O:20]>O.C(O)C>[CH2:18]([O:16][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH:18][C:19](=[O:20])[CH:21]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:1][CH:2]3[O:4][CH2:3]3)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)[CH:19]1[O:20][CH2:21]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 113447983-Methoxy-4-(2-oxiranylmethoxy)benzaldehyde

Product 1

HCID 1084821,5-bis[4-(2,3-epoxypropyloxy)phenyl]penta-1,4-dien-3-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

p-Glycidyloxybenzaldehyde (80 g; prepared according to Method B) in acetone (13 g) and ethanol (80 g) was added over 1 hour to a stirred solution of sodium hydroxide (9 g) in a mixture of water (90 g) and ethanol (80 g), keeping the temperature at 25° to 30° C. On complete addition the mixture was stirred at 25° to 30° C. for a further hour, then filtered. The residue was dissolved in epichlorohydrin (400 ml), washed at 60° C. with 5% aqueous sodium hydrogen sulfate (100 ml), then with water (200 ml). The solution was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give 1,5-bis(p-glycidyloxyphenyl)-1,4-pentadien-3-one. The yield was 58 g (68% of theoretical yield) and the product had an epoxide content of 4.5 equivalents/kg (theoretical value 5.29 equivalents/kg). On recrystallisation from ethanol the epoxide content of the product was 5.18 equivalents/kg. This product was shown to be identical with an authentic sample of 1,5-bis(p-glycidyloxyphenyl)-1,4-pentadien-3-one by gel permeation chromatography and by NMR, UV, and IR spectral analysis.

Workup

  1. customat 25° to 30° C
  2. additionOn complete addition the mixture
  3. filtrationfiltered
  4. dissolutionThe residue was dissolved in epichlorohydrin (400 ml)
  5. washwashed at 60° C. with 5% aqueous sodium hydrogen sulfate (100 ml)
  6. dry with materialThe solution was dried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-14365e251b4e43f09f37c344b650140e
Source dataset
uspto-grants-1981_08
Patent number
US04282353

Reaction notes

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