Acetic Acid → 3-Formylbut-2-enyl acetate

HRID 21848

Reaction equation

HRID 21848 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5]C=C[CH:2]=1.[C:8]([OH:11])(=[O:10])[CH3:9].[OH2:12]>>[C:8]([O:11][CH2:5][CH:6]=[C:1]([CH3:7])[CH:2]=[O:12])(=[O:10])[CH3:9]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 1140Toluene

Product 1

HCID 846993-Formylbut-2-enyl acetateYield 74%

Conditions

Temperature
75 °C

Procedure

4-Acetoxy-2-methyl-1-chloro-2-butene (7.8 g) was added to a suspension of hexamethylenetetramine (6.7 g) in acetonitrile (47 ml), and the mixture was stirred at room temperature for 16 hours. The resulting crystals were separated by filtration to give crystals (12.5 g) of the quaternary ammonium salt. The salt (7.9 g) was dissolved in water (50 ml), and toluene (100 ml) was added. Acetic acid (1.5 g per addition) was added 30 minutes, 1 hour and 2 hours after the beginning of the reaction with stirring at 75° C. The reaction was stopped 6 hours after the beginning of the reaction. The toluene layer was separated and concentrated. The remaining oil was purified by silica gel column chromatography to give 4-acetoxy-2-methyl-2-buten-1-al (2.6 g, 74%).

Workup

  1. customafter the beginning of the reaction
  2. customafter the beginning of the reaction
  3. customThe toluene layer was separated
  4. concentrationconcentrated
  5. customThe remaining oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d554762e6a2f46829719a1c5b6aee6ba
Source dataset
uspto-grants-1995_06
Patent number
US05424478

Linked notes

Loading…