Sulfuric Acid → 3-Formylbut-2-enyl acetate

HRID 21849

Reaction equation

HRID 21849 reaction equation
[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:10])[CH2:8]Cl)(=[O:3])[CH3:2].C1N2CN3CN(C2)CN1C3.S(=O)(=O)(O)[OH:22]>O>[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:10])[CH:8]=[O:22])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 534009324-Chloro-3-methylbut-2-en-1-yl acetate

Product 1

HCID 846993-Formylbut-2-enyl acetateYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

Crude 4-acetoxy-2-methyl-1-chloro-2-butene (194 g, Purity: 83.8%, 1 mol) was added to hexamethylenetetramine (168 g, 1.2 mol)/water (1 liter), and the mixture was stirred at 35° C. for 4 hours and then separated into aqueous and organic layers. 1,2-Dichloroethane (1 liter) was added to the aqueous layer, the mixture was subjected to reaction at 72° C. for 6 hours while adjusting the pH with 1N sulfuric acid. The 1,2-dichloroethane layer was separated, 1,2-dichloroethane (1 liter) was added, and the reaction was carried out again. The 1,2-dichloroethane layers were combined and concentrated. The residue was distilled under reduced pressure to give 4-acetoxy-2-methyl-2-buten-1-al (98 g, 69%). bp.0.2-0.3 : 58°-66° C.

Workup

  1. customseparated into aqueous and organic layers
  2. addition1,2-Dichloroethane (1 liter) was added to the aqueous layer
  3. customthe mixture was subjected to reaction at 72° C. for 6 hours
  4. customThe 1,2-dichloroethane layer was separated
  5. addition1,2-dichloroethane (1 liter) was added
  6. concentrationconcentrated
  7. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-aab0f7af60384a74ae6c7680925421cb
Source dataset
uspto-grants-1995_06
Patent number
US05424478

Linked notes

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