1,5-Dihydroxynaphthalene → 1,5-Bis(vinyloxy)naphthalene

HRID 15689

Reaction equation

HRID 15689 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].OC1C2C(=C(O)C=CC=2)C=CC=1.[C:19]([O:22][CH:23]=[CH2:24])(=O)[CH3:20].OC1C2[C:30](=[C:31]([O:36][CH:37]=[CH2:38])[CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[CH:23]([O:22][C:19]1[C:20]2[C:30](=[C:31]([O:36][CH:37]=[CH2:38])[CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1)=[CH2:24]

Participants

6

Reactant 4

HCID 67491,5-DihydroxynaphthaleneHCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 229357751-Hydroxy-5-vinyloxynaphthalene

Product 1

HCID 103308051,5-Bis(vinyloxy)naphthalene

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 1,5-dihydroxynaphthalene (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-hydroxy-5-vinyloxynaphthalene and 1,5-bis(vinyloxy)naphthalene were formed in yields of 15% and 13%, respectively, with a conversion from 1,5-dihydroxynaphthalene of 30%.

Sources & evidence

ORD record
ord-dd53c2c1da69404aa57a66b9f869458b
Source dataset
uspto-grants-2010_06
Patent number
US07732645B2

Linked notes

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