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

HRID 1109254Notes

Reaction equation

HRID 1109254 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>[Co].C(O)(C)C>[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

4

Reactant 1

HCID 3094320Oxacyclohexadecane-2,13-dione

Product 1

HCID 309431913-Hydroxy-oxacyclohexadecan-2-oneYield 95.2%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 3776IsopropanolSolvent

Procedure

480 g (1.89 mol) of 12-oxo-15-pentadecanolide (VI) are mixed with 1,000 g of isopropanol and hydrogenated in an autoclave with addition of 9.6 g of Raney cobalt under a hydrogen pressure of 100 bar at 135° C. After the solvent has been stripped off, distillation of the residue gives 460 g (1.80 mol) of 12-hydroxy-15-pentadecanolide.

Workup

  1. distillationdistillation of the residue

Sources & evidence

ORD record
ord-fcba679ea5e94575a5593701b871ce4f
Source dataset
uspto-grants-1994_06
Patent number
US05319104

Reaction notes

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