Isobutyraldehyde → HCID 178436228, compound

HRID 1897626Notes

Reaction equation

HRID 1897626 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].[CH:12](=O)[CH:13]([CH3:15])[CH3:14]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1/[N:5]=[CH:12]/[CH:13]([CH3:15])[CH3:14])[CH3:2]

Participants

5

Reactant 2

HCID 6561IsobutyraldehydeHCID 113692,6-Diethylaniline

Product 1

HCID 178436228HCID 178436228, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

Benzene (150 mL) was added to 2,6-diethylaniline (18.59 g, 124.6 mmol) and 3 angstrom molecular sieves (ca. 50 mL). Isobutyraldehyde (9.43 g, 131 mmol) and p-toluenesulfonic acid monohydrate (20 mg, 0.011 mmol) were then added. The flask was sealed and heated to 50° C. After stirring overnight the very pale yellow solution was filtered and the volatiles were removed under reduced pressure to afford 22.5 g of compound A (84.6%) as a clear, pale yellow oil.

Workup

  1. customThe flask was sealed
  2. filtrationwas filtered
  3. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-355b4cc6b1254fd0ad0d63455e5d21af
Source dataset
uspto-grants-2013_08
Patent number
US08519147B2

Reaction notes

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