Oxygen → HCID 17798952, compound

HRID 351319Notes

Reaction equation

HRID 351319 reaction equation
[CH3:1][CH:2]([OH:4])C.ON1C(=O)C2=CC=CC=C2C1=O.O=O.[OH:19][CH:20]1[CH:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:24]([CH3:33])([CH3:32])[O:23][C:21]1=[O:22]>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(#N)C>[OH:19][CH:20]([CH:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:24]([OH:23])([CH3:33])[CH3:32])[C:21]([O:4][CH2:2][CH3:1])=[O:22]

Participants

7

Reactant 4

HCID 977OxygenHCID 3776IsopropanolHCID 10665N-HydroxyphthalimideHCID 18436228HCID 18436228, compound

Product 1

HCID 17798952HCID 17798952, compound

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3 mmol of diethyl cinnamate, 3 ml of 2-propanol, 0.6 mmol of N-hydroxyphthalimide, 0.015 mmol of cobalt(II) acetate, 0.03 mmol of acetylacetonatocobalt(III), and 1 ml of acetonitrile was stirred at 70° C. in an oxygen atmosphere (1 atm) for 12 hours. A gas chromatographic analysis of products in a reaction mixture revealed that α-hydroxy-β-phenyl-γ,γ-dimethyl-γ-butyrolactone and ethyl 2,4-dihydroxy-4-methyl-3-phenylpentanoate were formed in yields of 18% and 24%, respectively. The conversion rate from diethyl cinnamate was 61%.

Sources & evidence

ORD record
ord-d4aab64c63e4405c93d369da39f9dbb6
Source dataset
uspto-grants-2007_02
Patent number
US07183423B1

Reaction notes

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