Acetic Acid → HCID 54218658, compound

HRID 1981475Notes

Reaction equation

HRID 1981475 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[H][H].C(O)(=O)C.[C:20]([O:23][CH:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:25])(=[O:22])[CH3:21]>O>[CH3:3][N:4]([CH3:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:21][C:20]([O:23][CH:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:25])=[O:22])=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 74794-(Dimethylamino)BenzaldehydeHCID 24758Sodium hydrideHCID 979872-Octanol, 2-acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 54218658HCID 54218658, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (1.9 g of an 80% dispersion in oil) was added portionwise with stirring over 0.5 hour to 4-dimethylaminobenzaldehyde (7.46 g) in 2-octyl acetate (153 g) at 25° C. The temperature was raised until a steady evolution of hydrogen began (100° C.) and held at this temperature for eight hours. The cooled mixture was treated with glacial acetic acid (4 ml) and then water (50 ml) added. The upper layer was separated, washed with 10% sodium carbonate solution, water, and dried (MgSO4). The excess of 2-octyl acetate was removed by distillation at 15 mm pressure, and the residue fractionated under high vacuum, yielding 7.3 g 2-octyl 4-dimethylaminocinnamate as a pale amber viscous oil, b.p. 194°-200° C./0.25 mm. After freezing it remelted at -11° C.

Workup

  1. custom(100° C.)
  2. customThe upper layer was separated
  3. washwashed with 10% sodium carbonate solution, water
  4. dry with materialdried (MgSO4)
  5. customThe excess of 2-octyl acetate was removed by distillation at 15 mm pressure

Sources & evidence

ORD record
ord-1dff30d49fc249c89ffe36666328ccd4
Source dataset
uspto-grants-1986_06
Patent number
US04592906

Reaction notes

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