Cyclododecanone → Cyclopentadecanone

HRID 2083439Notes

Reaction equation

O=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](O)=O)[CH2:3][CH2:4][C:5]([OH:7])=O.[C:21]1(=[O:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[C:5]1(=[O:7])[CH2:4][CH2:3][CH2:2][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.[C:21]1(=[O:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

Reactant 2

HCID 13246Cyclododecanone2×

HCID 203585974-Oxo-pentadecanedioic acid2×

Product 2

HCID 10409Cyclopentadecanone

HCID 13246Cyclododecanone

Procedure

4-oxo-pentadecanedioic acid IV is obtainable at the yield of 66.2% based on the moles of cyclododecanone through the referential examples 1 and 2 and Example 1 as mentioned later. Alternatively, the compound IV is obtainable at the yield of 60.8% based on the moles of cyclododecanone through Examples 5 and 7. Further combined with the Referential Example 3, the overall yields of cyclopentadecanone from cyclododecanone are 39.7% and 36.4%, respectively. This fact shows that this invention provides increased yield as another improved advantage in addition to the before-mentioned advantage of avoiding employment of polyphosphoric acid for conversion to ketone.

Sources & evidence

ORD record: ord-ee0def43c6dd418581c6e0752d1e001c
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04085274

Reaction notes

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