P-Xylene → 4'-Acetoxy-3,5-bis(methoxymethoxy)stilbene

HRID 78868

Reaction equation

CC1C=CC(C)=CC=1.[CH3:9][O:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][CH2:23][O:24][CH3:25])[CH:21]=1)[C:16](Cl)=O.[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].CN1CCOCC1>[Pd].[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:26]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[CH:16][C:15]2[CH:14]=[C:13]([O:12][CH2:11][O:10][CH3:9])[CH:21]=[C:20]([O:22][CH2:23][O:24][CH3:25])[CH:19]=2)=[CH:32][CH:31]=1)(=[O:28])[CH3:27]

Participants

Conditions

Temperature: 120 °C

Procedure

A 50 mL round bottom flask was charged with p-xylene (20 mL), Pd II catalyst (22.5 mg, 0.1 mmol), 1,3-bis-(2,6-diisopropylphenyl)imidazolinium chloride (42.7 mg, 0.1 mmol), 3,5-bis(methoxymethoxy)benzoyl chloride (2.42 g, 10 mmol), 4-acetoxystyrene (1.94 g, 12 mmol), and N-methyl morpholine (1.38 g, 12 mmol). The mixture was stirred at 120° C. for 3.5 h under 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 and gave the product (2.1 g, 59%) as white solid. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.48 (d, 2H), 7.08-6.93 (m, 4H), 6.86 (d, 2H), 6.66 (t, 1H), 5.19 (s, 4H), 3.50 (s, 6H), 2.30 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ 169.5, 158.7, 150.3, 139.5, 135.0, 128.7, 128.5, 127.6, 121.9, 108.0, 104.5, 94.6, 56.2, 21.2; HRMS (EI+) found 358.1409 M+, calcd 358.1416 for C20H22O6.

Workup

temperatureThen it was cooled to room temperature
filtrationfiltered
washThe filtrate was washed with brine
dry with materialdried over Na2SO4
filtrationThen it was filtered
custompurified via flash chromatography

Sources & evidence

ORD record: ord-5b51ffe1e38f4bf6b9190d2f7627fc7a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841477B2

Linked notes

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