3',4'-Dimethoxycinnamic acid → (E)-3-(cinnamoyloxy)-2-hydroxypropyl 3-(3,4-dimethoxyphenyl)acrylate

HRID 2174424Notes

Reaction equation

HRID 2174424 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8]([OH:10])=[O:9].[C:16]([O:26][CH2:27][CH:28]1[O:30][CH2:29]1)(=[O:25])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:29][CH:28]([OH:30])[CH2:27][O:26][C:16](=[O:25])/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:9])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

5

Reactant 2

HCID 168483',4'-Dimethoxycinnamic acid2×HCID 53975804HCID 53975804, compound

Product 1

HCID 68159296(E)-3-(cinnamoyloxy)-2-hydroxypropyl 3-(3,4-dimethoxyphenyl)acrylate

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 312751,4-DioxaneSolvent

Procedure

3,4-dimethoxy cinnamic acid (140; 3.82 g; 18.37 mol) was dissolved in 60 mL of dioxane and heated under reflux (60°-70° C.). A catalytic amount (22.5 mg; 0.7 mmol) of tetrabutylammonium bromide and 1.5 g (7.35 mmol) of glycidyl cinnamate (130) were consecutively added to the solution of 3,4-dimethoxy cinnamic acid (140). The resulting mixture was heated to 100°-105° C. with continuous stirring for 15-16 h and then distilled under reduced pressure to yield compound (Id). 1H-NMR (CD3OD) δ 3.81 (s, 3H), 3.83 (s, 3H), 4.14 (m, 1H), 4.27 (d, 4H, J=8 Hz), 6.42 (d, 1H, J=16 Hz), 7.64 (d, 1H, J=16 Hz), 7.15 (dd, 1H, J=8 Hz, 2 Hz), 6.92 (d, 1H, J=8 Hz), 7.18 (d, 1H, J=2 Hz), 6.53 (d, 1H, J=16 Hz), 7.70 (d, 1H, J=16 Hz), 7.35 (m, 3H), 7.56 (m, 2H)

Workup

  1. temperatureheated
  2. temperatureunder reflux (60°-70° C.)
  3. temperatureThe resulting mixture was heated to 100°-105° C.
  4. distillationdistilled under reduced pressure
  5. customto yield compound (Id)

Sources & evidence

ORD record
ord-ac10817d7cb3452a9bc2ca6d3c7dc109
Source dataset
uspto-grants-2015_06
Patent number
US09061993B2

Reaction notes

Loading…