Phloroglucinol → 1,3,5-Tris(vinyloxy)benzene

HRID 15688

Reaction equation

HRID 15688 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].OC1C=C(O)C=C(O)C=1.[C:16]([O:19][CH:20]=[CH2:21])(=O)[CH3:17].OC1C=C(OC=C)C=C(O)C=1.OC1[CH:39]=[C:38]([O:40][CH:41]=[CH2:42])[CH:37]=[C:36]([O:43][CH:44]=[CH2:45])C=1>C1(C)C=CC=CC=1>[CH:20]([O:19][C:16]1[CH:17]=[C:36]([O:43][CH:44]=[CH2:45])[CH:37]=[C:38]([O:40][CH:41]=[CH2:42])[CH:39]=1)=[CH2:21]

Participants

7

Reactant 5

HCID 359PhloroglucinolHCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 229357621-Hydroxy-3,5-bis(vinyloxy)benzeneHCID 229358141,3-Dihydroxy-5-vinyloxybenzene

Product 1

HCID 118202261,3,5-Tris(vinyloxy)benzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (67 mg, 0.1 mmol) and sodium carbonate (640 mg, 6 mmol) in toluene (5 ml) were added 1,3,5-trihydroxybenzene (5 mmol) and vinyl acetate (2.15 g, 25 mmol), followed by stirring at 100° C. in an atmosphere of argon gas for 6 hours. The reaction mixture was analyzed by gas chromatography to find that 1,3-dihydroxy-5-vinyloxybenzene, 1-hydroxy-3,5-bis(vinyloxy)benzene, and 1,3,5-tris(vinyloxy)benzene were formed in yields of 5%, 4%, and 18%, respectively, with a conversion from 1,3,5-trihydroxybenzene of 29%.

Sources & evidence

ORD record
ord-8ef2f81780604f299e5c56be6d35d965
Source dataset
uspto-grants-2010_06
Patent number
US07732645B2

Linked notes

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