P-Xylene → Resveratrol triacetate

HRID 2236337

Reaction equation

HRID 2236337 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) 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-aa7333d3f8f449b99f93e3f5ae7e9a63
Source dataset
uspto-grants-2010_05
Patent number
US07714161B2

Linked notes

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