HCID 23694762, compound → HCID 67111077, compound

HRID 2174427Notes

Reaction equation

HRID 2174427 reaction equation
[C:1]([O-:13])(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.[Na+].[C:15]([O:25][CH2:26][CH:27]1[O:29][CH2:28]1)(=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(C)=O>[OH:7][C:6]1[CH:5]=[C:4]([CH:3]=[CH:2][C:1]([O:13][CH2:28][CH:27]([OH:29])[CH2:26][O:25][C:15](=[O:24])/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:12])[CH:11]=[CH:10][C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 23694762HCID 23694762, compoundHCID 53975804HCID 53975804, compound

Product 1

HCID 67111077HCID 67111077, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of sodium caffeate (210; 7.35 mmol) in DMSO (20 mL) at 60°-70° C. was added glycidyl cinnamate (130; 7.35 mmol). The resulting mixture was heated to 60°-75° C. with continuous stirring for 22-24 h and then distilled under reduced pressure to yield compound (Ie). 1H-NMR (CD3OD) δ 4.16 (s, 1H), 2.28 (s, 4H), 6.29 (d, 1H, J=16 Hz), 6.65 (d, 1H, J=16 Hz), 6.75 (d, 1H, J=8 Hz), 6.93 (1H, dd, J=8, 2 Hz), 7.03 (d, 1H, J=2 Hz), 7.37 (m, 1H), 7.38 (m, 1H), 7.55 (m), 7.59 (d, 1H, J=16 Hz), 7.72 (d, 1H, J=16 Hz).

Workup

  1. temperatureThe resulting mixture was heated to 60°-75° C.
  2. distillationdistilled under reduced pressure
  3. customto yield compound (Ie)

Sources & evidence

ORD record
ord-f2d36a0a84da45afbd938730bee537db
Source dataset
uspto-grants-2015_06
Patent number
US09061993B2

Reaction notes

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