Formaldehyde → HCID 22479028, compound

HRID 2086899Notes

Reaction equation

HRID 2086899 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[CH2:12]=O.Cl.[CH3:15][NH:16][CH3:17]>CO.O>[CH3:15][N:16]([CH3:12])[CH2:17][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:9](=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 1374281-(4-Methylphenyl)propan-2-one

Product 1

HCID 22479028HCID 22479028, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-methylphenylacetone (3.01 g), paraformaldehyde (0.489 g) and dimethylamine hydrochloride (1.49 g) in MeOH (2 ml) is stirred under reflux for 3 h. The reaction mixture is diluted with 20 ml of water and the product is extracted with two portions of ether. After addition of 1 M aqueous NaOH solution, the aqueous layer is extracted with two more portions of ether. The combined organic layers are dried (Na2SO4) and the solvent is evaporated to obtain 4-dimethylamino-3-p-tolyl-butan-2-one (compound of formula VI) as a yellowish liquid, MS (ISP) 206.2 (M+H)+. 4-Dimethylamino-3-p-tolyl-butan-2-one is dissolved in AcOEt (17 ml) and iodomethane (1.46) is added. After 1 h the formed solid is collected by filtration, washed with AcOEt and dried on the vacuum. 2.61 g of trimethyl-(3-oxo-2-p-tolyl-butyl)-ammonium iodide are obtained as an off-white solid, MS (ISP) 220.3 M+.

Workup

  1. temperatureunder reflux for 3 h
  2. extractionthe product is extracted with two portions of ether
  3. additionAfter addition of 1 M aqueous NaOH solution
  4. extractionthe aqueous layer is extracted with two more portions of ether
  5. dry with materialThe combined organic layers are dried (Na2SO4)
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-951e7160c5134f9f911d669d86e77671
Source dataset
uspto-grants-2004_04
Patent number
US06727261B2

Reaction notes

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