Oxygen → HCID 14342860, compound

HRID 351323Notes

Reaction equation

HRID 351323 reaction equation
[C:1]([O:5]C)(=[O:4])[CH:2]=[CH2:3].[CH2:7]([OH:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH:14]N1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=O.O=O.[C:28](#N)[CH3:29]>C([O-])(=O)C.[Co+2].C([O-])(=O)C>[OH:20][CH:19]1[CH2:18][CH:21]([CH2:22][CH2:23][CH2:24][CH2:17][CH3:16])[O:5][C:1]1=[O:4].[C:7]([CH2:3][CH:2]([OH:14])[C:1]([O:5][CH2:28][CH3:29])=[O:4])(=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

8

Reactant 5

HCID 977OxygenHCID 6342AcetonitrileHCID 7294Methyl AcrylateHCID 81031-HexanolHCID 10665N-Hydroxyphthalimide

Product 2

HCID 14342860HCID 14342860, compoundHCID 18436245HCID 18436245, compound

Reagents, catalysts & solvents 1

HCID 6277Cobalt diacetateCatalyst

Procedure

A mixture of 3 mmol of methyl acrylate, 30 mmol of hexanol, 0.6 mmol of N-hydroxyphthalimide, 0.003 mmol of cobalt(II) acetate, 0.03 mmol of acetylacetonatocobalt(III), and 1 ml of acetonitrile was stirred at 60° C. in an oxygen atmosphere (1 atm) for 5 hours. A reaction mixture was subjected to column chromatography on a silica gel to yield α-hydroxy-γ-pentyl-γ-butyrolactone in a yield of 46% and ethyl β-hexanoyl-α-hydroxypropionate in a yield of 40%.

Sources & evidence

ORD record
ord-8259b3d6a7f54dffa3351ded91f33320
Source dataset
uspto-grants-2007_02
Patent number
US07183423B1

Reaction notes

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