Acetone → 4-(1,3-Benzodioxol-5-yl)but-3-en-2-one

HRID 1980790Notes

Reaction equation

HRID 1980790 reaction equation
[OH-].[Na+].[CH:3]1[C:8]([CH:9]=O)=[CH:7][C:6]2[O:11][CH2:12][O:13][C:5]=2[CH:4]=1.[CH3:14][C:15]([CH3:17])=[O:16]>O>[CH2:12]1[O:13][C:5]2[CH:4]=[CH:3][C:8]([CH:9]=[CH:14][C:15](=[O:16])[CH3:17])=[CH:7][C:6]=2[O:11]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 8438PiperonalHCID 14798Sodium Hydroxide

Product 1

HCID 184804-(1,3-Benzodioxol-5-yl)but-3-en-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An aqueous solution of 10% sodium hydroxide (3.5 ml) was added dropwise to a solution of piperonal (20.0 g) in acetone (27 ml) and water (14 ml), the temperature of the reaction mixture being maintained below 30° C. during the addition. On completion of the reaction (ca 2 hr) the reaction mixture was poured into water and the precipitate was filtered off and dried to give 1-(3,4-methylenedioxyphenyl)but-1-en-3-one as a crystalline solid, mp 108° C. (from ethanol).

Workup

  1. temperaturethe temperature of the reaction mixture being maintained below 30° C. during the addition
  2. customOn completion of the reaction (ca 2 hr) the reaction mixture
  3. filtrationthe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-8af3041d0b5f4e11be69f67457444873
Source dataset
uspto-grants-1985_04
Patent number
US04511391

Reaction notes

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