P-Xylene → Resveratrol triacetate

HRID 78876

Reaction equation

HRID 78876 reaction equation
CC1C=CC(C)=CC=1.[C:9]([O:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][C:23](=[O:25])[CH3:24])[CH:21]=1)[C:16](Cl)=O)(=[O:11])[CH3:10].[C:26]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=C)=[CH:32][CH:31]=1)(=[O:28])[CH3:27]>CC([O-])=O.CC([O-])=O.[Pd+2].[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C.CCOC(C)=O>[C:9]([O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:34][C:33]2[CH:36]=[CH:37][C:30]([O:29][C:26](=[O:28])[CH3:27])=[CH:31][CH:32]=2)[CH:19]=[C:20]([O:22][C:23](=[O:25])[CH3:24])[CH:21]=1)(=[O:11])[CH3:10]

Participants

7

Reactant 3

HCID 7809P-XyleneHCID 758214-Ethenylphenyl acetateHCID 11368883(3-Acetyloxy-5-carbonochloridoylphenyl) acetate

Product 1

HCID 3935161Resveratrol triacetateYield 70.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 184547821,3-BIS(2,6-DIISOPROPYLPHENYL)imidazoLIDINIUM-CHLORIDECatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A 100 mL round bottom flask was charged with p-xylene (56 mL), Pd(OAc)2 (62.86 mg, 0.28 mmol), 1,3-bis-(2,6-diisopropylphenyl)imidazolinium chloride (119.53 mg, 0.28 mmol), 3,5-diacetoxybenzoyl chloride (7.19 g, 28 mmol), 4-acetoxystyrene (5.35 mL, 33.6 mmol), and N-methyl morphorline (4.2 mL, 33.6 mmol). The mixture was stirred at 120° C. for 3.5 h at nitrogen atmosphere. Then it was cooled to room temperature and EtOAc was added and filtered. The filtrate was washed with brine and dried over Na2SO4. Then it was filtered and purified via flash chromatography (15% EtOAc/hexane, 25% EtOAc/Hexene, then 35% EtOAc/hexane) and gave resveratrol triacetate (6.95 g, 70.1%) as white solid. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.50 (d, 2H), 7.12-6.94 (m, 6H), 6.82 (t, 1H), 2.31 (s, 9H); 13C NMR (CDCl3, 75 MHz) δ 169.6, 169.2, 151.5, 150.6, 139.7, 134.7, 129.9, 127.9, 127.4, 122.1, 117.1, 114.6, 21.4; mp=116-118° C.; HRMS (EI+) found 354.1118 M+, calcd 354.1103 for C20H18O6; Anal. Calcd for C20H18O6: C, 67.79; H, 5.12. Found: C, 67.93; H, 5.26.

Workup

  1. temperatureThen it was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationThen it was filtered
  6. custompurified via flash chromatography (15% EtOAc/hexane, 25% EtOAc/Hexene

Sources & evidence

ORD record
ord-365d42bfa5d54c95a435f5b1e2f230ca
Source dataset
uspto-grants-2014_09
Patent number
US08841477B2

Linked notes

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