Oxacyclohexadecane-2,13-dione → 13-Hydroxy-oxacyclohexadecan-2-one

HRID 613224Notes

Reaction equation

HRID 613224 reaction equation
[O:1]=[C:2]1[CH2:18][CH2:17][CH2:16][O:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>[Ni]>[OH:1][CH:2]1[CH2:18][CH2:17][CH2:16][O:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 3094320Oxacyclohexadecane-2,13-dione

Product 1

HCID 309431913-Hydroxy-oxacyclohexadecan-2-one

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

According to Russian Inventor's Certificate 1 133 274, 12-oxo-15-pentadecanolide is reduced in the presence of Raney nickel to give 12-hydroxy-15-pentadecanolide, which is then dehydrated, for example in the presence of phosphoric acid, to give the corresponding 15-pentadec-11- and -12-enolides, and these products are then hydrogenated in the presence of a nickel catalyst to give I.

Sources & evidence

ORD record
ord-87fa978109fb4f6bae4b5c0f6f6dafd0
Source dataset
uspto-grants-1999_12
Patent number
US06008185

Reaction notes

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