Octanoic Acid → HCID 10573853, compound

HRID 2393911Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:30][O:29][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH:18]=[C:19]6[CH2:24][C@@H:23]([OH:25])[CH2:22][CH2:21][C@:20]6([CH3:26])[C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H:6]2[CH3:28])[CH2:4][CH2:3]1.C(O)(=O)CCCCCCC.C(OC(=O)C)(=O)C>>[CH3:28][C:6]1[C@@H:7]2[C@:12]3([CH3:27])[C@@H:11]([CH2:10][C@@H:8]2[O:9][C:5]=1[CH2:4][CH2:3][C@H:2]([CH2:30][OH:29])[CH3:1])[C@@H:16]1[CH2:17][CH:18]=[C:19]2[CH2:24][C@@H:23]([OH:25])[CH2:22][CH2:21][C@:20]2([CH3:26])[C@H:15]1[CH2:14][CH2:13]3

Participants

Reactant 3

HCID 379Octanoic Acid

HCID 7918Acetic Anhydride

HCID 99474Diosgenin

Product 1

HCID 10573853HCID 10573853, compoundYield 87%

Procedure

In a study of the degradation of a number of sapogenins at the Glaxo Laboratorties in UK, good results were obtained by heating diosgenin in refluxing n-Octanoic acid (bp 237° C.) containing acetic anhydride, distilling off the low boiling fraction until the temperature reached 270° C. and refluxing for 2 hours followed by saponifications resulting in the production of pseudodiosgenin in a yield of 87% (Ref:Cameroon AFB, Evans RM, Hamlet JC, Hunt JS, Jones PG and Long AG, J Chem Soc, 2807 1955.)

Workup

customwere obtained
distillationdistilling off the low boiling fraction until the temperature
customreached 270° C.
temperaturerefluxing for 2 hours

Sources & evidence

ORD record: ord-2aa1abb629094c3883f939306cbd0423
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05808117

Reaction notes

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