Paeonol → 3-(Dimethylamino)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one

HRID 1694643Notes

Reaction equation

HRID 1694643 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>>[CH3:15][N:16]([CH3:18])[CH:17]=[CH:11][C:10]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[OH:1])=[O:12]

Participants

3

Reactant 2

HCID 11092PaeonolHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 672789663-(Dimethylamino)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one

Conditions

Temperature
90 °C

Procedure

A mixture of 1-(2-hydroxy-4-methoxyphenyl)ethane-1-one (20 g, 120 mmol) and N,N-dimethylformamide dimethylacetal (23 g, 181 mmol) was stirred at 90° C. for 2 hours. After cooling to room temperature the reaction mixture provided a yellow precipitate, which was washed with ethyl acetate (3×30 ml), water (2×50 ml), and dried under reduced pressure to yield 3-(dimethylamino)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one (9) as the trans isomer; MS 222.1 (M+H)

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customprovided a yellow precipitate, which
  3. washwas washed with ethyl acetate (3×30 ml), water (2×50 ml)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-6f2f0c90a13b4826b118cb642c34f0a0
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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