Acetaldehyde → HCID 12370021, compound

HRID 1657873Notes

Reaction equation

HRID 1657873 reaction equation
[CH:1](=O)[CH3:2].B(F)(F)F.CCO[CH2:11][CH3:12].[OH-].[NH4+].[CH3:15][N:16]([CH3:25])[CH2:17][CH:18]1[CH2:23][O:22][CH:21]([CH3:24])[O:20][CH2:19]1.[C:26](#N)[CH3:27]>O>[CH3:15][N:16]([CH3:25])[CH:17]([C:2]1[CH:1]=[CH:12][CH:11]=[CH:27][CH:26]=1)[CH:18]1[CH2:19][O:20][CH:21]([CH3:24])[O:22][CH2:23]1

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 6342AcetonitrileHCID 8000Boron trifluoride etherateHCID 14923Ammonium HydroxideHCID 21530553HCID 21530553, compound

Product 1

HCID 12370021HCID 12370021, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(α-Dimethylamino)benzyl-1,3-propanediol, 2.5 g. (0.012 mole), was dissolved in 25 ml. of acetonitrile. Water, 7.68 g. (0.48 mole), 10 ml. of acetaldehyde and 3.01 ml. (0.024 mole) of boron trifluoride etherate were added to the reaction mixture and the mixture was allowed to stir overnight. The reaction mixture was heated on the steam bath for 1 hour. The cooled mixture was poured into ammonium hydroxide and the basic mixture was extracted with ether. The ether extract was washed with water, dried over magnesium sulfate and evaporated to a solid residue. The solid was recrystallized from hexane to yield 0.44 g. of N,N,2-trimethyl-m-dioxane-5-methylamine, mp about 140°-143° C.

Workup

  1. dissolution(0.012 mole), was dissolved in 25 ml
  2. temperatureThe reaction mixture was heated on the steam bath for 1 hour
  3. extractionthe basic mixture was extracted with ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to a solid residue
  8. customThe solid was recrystallized from hexane
  9. customto yield 0.44 g

Sources & evidence

ORD record
ord-b74849dd1e8c456389acbd06a008d211
Source dataset
uspto-grants-1976_06
Patent number
US03962269

Reaction notes

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