Isopropanol → 2-Bromo-3-isopropoxy-propenal

HRID 732110

Reaction equation

HRID 732110 reaction equation
[Br:1][CH:2]([CH:5]=[O:6])[CH:3]=[O:4].O.[C:8]1(C)[CH:13]=CC(S(O)(=O)=O)=C[CH:9]=1.CC(O)C>C1CCCCC1>[Br:1][C:2](=[CH:5][O:6][CH:8]([CH3:13])[CH3:9])[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 749452-BromopropanedialHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 534166342-Bromo-3-isopropoxy-propenal

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
86 °C

Procedure

A mixture of 2-bromomalonaldehyde, para-toluenesulfonic acid monohydrate, 2-propanol and cyclohexane were stirred at 86° C. in flask with a dean-stark trap under azeotropic conditions. Further distillation removed another 40% of the original solvent volume. The mixture was cooled to 0° C., then concentrated in-vacuo, to isolate the title compound (13.2 g). 1H-NMR: 9.16 (s, 1H), 7.65 (s, 1H), 4.51 (m, 1H), 1.47 (d, 6H).

Workup

  1. distillationFurther distillation
  2. customremoved another 40% of the original solvent volume
  3. temperatureThe mixture was cooled to 0° C.
  4. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-e8d5ea4059e54f579482ffe59c821d7e
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Linked notes

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