Vinyl propanoate → 4-Hydroxy-2-vinyloxyphenyl phenyl ketone

HRID 15690

Reaction equation

HRID 15690 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[OH:7][C:8]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].[C:23](OC=C)(=O)[CH2:24]C.C1(C(C2C=CC(OC=C)=CC=2O)=O)C=CC=CC=1>C1(C)C=CC=CC=1>[C:12]1([C:10]([C:9]2[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:8]=2[O:7][CH:23]=[CH2:24])=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 7750Vinyl propanoateHCID 85722,4-DihydroxybenzophenoneHCID 10340Sodium CarbonateHCID 22935772[4-(Ethenyloxy)-2-hydroxyphenyl](phenyl)methanone

Product 1

HCID 229357934-Hydroxy-2-vinyloxyphenyl phenyl ketone

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 (1.27 g, 1.9 mmol) and sodium carbonate (24.9 g, 0.23 mol)) in toluene (280 ml) were added 2,4-dihydroxybenzophenone (40 g, 0.19 mol) and vinyl propionate (75.1 g, 0.75 mol), followed by stirring at 100° C. in an atmosphere of argon gas for 3 hours. The reaction mixture was analyzed by gas chromatography to find that 2-hydroxy-4-vinyloxyphenyl phenyl ketone [i.e., 2-hydroxy-4-vinyloxyphenyl(phenyl)methanone] and 4-hydroxy-2-vinyloxyphenyl phenyl ketone [i.e., 4-hydroxy-2-vinyloxyphenyl(phenyl) methanone] were formed in yields of 90% and 2%, respectively, with a conversion from 2,4-dihydroxybenzophenone of 99%.

Sources & evidence

ORD record
ord-444ed4c93c324f169126fe5d39585d30
Source dataset
uspto-grants-2010_06
Patent number
US07732645B2

Linked notes

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