Acetic Acid → HCID 11084099, compound

HRID 2243788Notes

Reaction equation

HRID 2243788 reaction equation
[C:1](O)(=O)C.O.[CH:6](=[O:15])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C=O>[CH2:1]=[C:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:6]=[O:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 31289Nonanal

Product 1

HCID 11084099HCID 11084099, compound

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Conditions

Temperature
50 °C

Procedure

A 5-liter flask fitted with an overhead stirrer and condenser was charged with di-N-butyl amine (61 g, 0.47 mol) and acetic acid (56 g, 0.9 mol). Roughly 900 ml of 37% formaldehyde solution in water (351 g formaldehyde, 11.7 mol) was then added and the resulting solution was heated to 50° C. with stirring. After this temperature was reached nonanal (1000 g, 7.0 mol) was fed in over about 2 h. A slight exotherm was noticed during the feed. Monitoring by GC showed the consumption of nonanal and the production of 2-methylene nonanal, finally reaching roughly 95% conversion after the addition was complete. The reaction mixture was allowed to cool to room temperature, poured into a separatory funnel, and washed once with 5% HCl solution. The organic layer was then washed once with saturated sodium bicarbonate, then taken directly on to the next step.

Workup

  1. customA 5-liter flask fitted with an overhead stirrer and condenser
  2. customwas fed in over about 2 h
  3. customthe consumption of nonanal
  4. additionafter the addition
  5. temperatureto cool to room temperature
  6. additionpoured into a separatory funnel
  7. washwashed once with 5% HCl solution
  8. washThe organic layer was then washed once with saturated sodium bicarbonate

Sources & evidence

ORD record
ord-c11e18af6e114d1f987dfa0c2997c926
Source dataset
uspto-grants-2010_03
Patent number
US07678749B2

Reaction notes

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