5-(2-(4-Hydroxyphenyl)Ethenyl)Benzene-1,3-Diol → HCID 76541001, compound

HRID 1914456Notes

Reaction equation

HRID 1914456 reaction equation
[C:1]1([CH:9]=[CH:10][C:11]2[CH:17]=[CH:16][C:14]([OH:15])=[CH:13][CH:12]=2)[CH:8]=[C:6]([OH:7])[CH:5]=[C:3]([OH:4])[CH:2]=1.[C:18](Cl)(=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>N1C=CC=CC=1>[C:18]([O:4][C:3]1[CH:2]=[C:1]([CH:9]=[CH:10][C:11]2[CH:17]=[CH:16][C:14]([O:15][C:18](=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:13][CH:12]=2)[CH:8]=[C:6]([O:7][C:18](=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:5]=1)(=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 50565-(2-(4-Hydroxyphenyl)Ethenyl)Benzene-1,3-Diol2×HCID 8206Palmitoyl chloride

Product 1

HCID 76541001HCID 76541001, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Resveratrol (100 mg; 0.44 mmol) was dissolved in 1 mL of pyridine. Palmitoyl chloride (425 μL; 1.40 mmol; 3.2 equiv) was added with immediate solid formation noted. This mixture was stirred at ambient temperature for 12 h at which point HPLC analysis indicated no resveratrol present. The mixture was partitioned into ethyl acetate and water and the water layer was decanted. The top organic layer was washed sequentially with 1.5 M HCl (10 mL) and 5% sodium bicarbonate (10 mL), dried (MgSO4), and concentrated to afford 0.45 g (99%) of resveratrol tripalmitate.

Workup

  1. customThe mixture was partitioned into ethyl acetate and water
  2. customthe water layer was decanted
  3. washThe top organic layer was washed sequentially with 1.5 M HCl (10 mL) and 5% sodium bicarbonate (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f54a3b3229b43c3b35999a53ed32abd
Source dataset
uspto-grants-2013_12
Patent number
US08613940B2

Reaction notes

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