Isobutyraldehyde → HCID 178436228, compound

HRID 561256Notes

Reaction equation

HRID 561256 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 3

HCID 6561IsobutyraldehydeHCID 113692,6-DiethylanilineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 178436228HCID 178436228, compound

Reagents, catalysts & solvents 1

HCID 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). Then isobutyraldehyde (9.43 g, 131 mmol) and p-toluenesulfonic acid monohydrate (20 mg, 0.011 mmol) were 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 the product as a clear, pale yellow oil. Yield: 22.5 g, 84.6%. 1H NMR (C6D6): δ 7.21 (1H, d), 7.02 (2H, m), 2.47 (4H, q), 2.39 (1H, m), 1.11 (6H, t), 1.01 (6H, d).

Workup

  1. customThe flask was sealed
  2. filtrationwas filtered
  3. customthe volatiles were removed under reduced pressure
  4. customto afford the product as a clear, pale yellow oil

Sources & evidence

ORD record
ord-624963315f9d4dfdbb5299821a180c50
Source dataset
uspto-grants-2011_11
Patent number
US08063232B2

Reaction notes

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