Acetic Acid → HCID 23080093, compound

HRID 2218556Notes

Reaction equation

HRID 2218556 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].[CH:7](=O)[CH2:8][CH2:9][CH2:10][CH3:11].O.C(O)(=O)C.[CH2:18]([NH:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:19]([CH3:21])[CH3:20]>>[CH3:20][CH:19]([CH3:21])[CH2:18][N:22]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 8063PentanalHCID 8085DiisobutylamineHCID 24083Sulfuric acid magnesium salt (1:1)2×

Product 1

HCID 23080093HCID 23080093, compoundYield 90.1%

Conditions

Temperature
12.5 °C

Procedure

To a suspension of magnesium sulfate (10.1 g) in diisobutylamine (72.0 g) was added dropwise valeraldehyde (24.6 g) at 0-5° C. under a nitrogen atmosphere, and it was stirred at 10-15° C. for 1 hour. After ice-cooling, water (60 ml) was added and it was stirred to dissolve the magnesium sulfate. After the removal of the aqueous layer, to the organic layer obtained was added a 9% (w/v) aqueous acetic acid solution (200 ml) at 0-5° C. and then stirred for 5 minutes. The aqueous layer was, then, removed again, a 0.5% (w/v) aqueous sodium hydroxide solution (60 ml) was added to the organic layer at 0-5° C., and stirred for 5 minutes. After stirring, the aqueous layer was removed to afford the title compound (51.3 g, yield: 80%, purity: 93.8%) as a colorless oil.

Workup

  1. temperatureAfter ice-cooling
  2. stirringit was stirred
  3. customAfter the removal of the aqueous layer
  4. customto the organic layer obtained
  5. stirringstirred for 5 minutes
  6. customremoved again
  7. additiona 0.5% (w/v) aqueous sodium hydroxide solution (60 ml) was added to the organic layer at 0-5° C.
  8. stirringstirred for 5 minutes
  9. stirringAfter stirring
  10. customthe aqueous layer was removed

Sources & evidence

ORD record
ord-7f315332d15f4c909d07286932bff484
Source dataset
uspto-grants-2008_08
Patent number
US07411095B2

Reaction notes

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