p-METHYLACETOPHENONE → HCID 13812977, compound

HRID 878524Notes

Reaction equation

HRID 878524 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.CO[C:13]([N:17]([CH3:19])[CH3:18])(OC)[CH3:14]>>[CH3:18][N:17]([CH3:19])/[C:13](/[CH3:14])=[CH:9]/[C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:10]

Participants

3

Reactant 2

HCID 8500p-METHYLACETOPHENONEHCID 878351,1-Dimethoxyethyl(dimethyl)amine

Product 1

HCID 13812977HCID 13812977, compoundYield 60%

Procedure

A solution of 1-(4-methylphenyl)ethanone (2.0 g, 15 mmol) in (1,1-dimethoxy-ethyl)-dimethyl-amine was heated to 120° C. and stirred overnight. The reaction mixture was cooled and concentrated to dryness. The residue was stirred with 25 mL hexane for 1 h and filtered. The solids were washed with hexane and then dried to give the title compound (1.8 g, 60%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 2.37 (3H, s), 2.65 (3H, s), 3.07 (6H, s), 5.68 (1H, s), 7.19 (2H, d, J=7.6 Hz), 7.77 (2H, d, J=8.0 Hz). [M+H] Calc'd for C13H17NO, 204; Found, 204.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated to dryness
  3. stirringThe residue was stirred with 25 mL hexane for 1 h
  4. filtrationfiltered
  5. washThe solids were washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-ecad8985e581466ebb07710fadc407ef
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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