Methanol → Dodecanedial

HRID 2293813Notes

Reaction equation

[CH:1]1C[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:13]=[O+][O-].O=O.O=[O+][O-].[CH3:21][OH:22]>>[CH:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:21]=[O:22]

Participants

Reactant 4

HCID 887Methanol

HCID 24823Ozone2×

HCID 53421619HCID 53421619, compound

HCID 131711318Oxygen ozone

Product 1

HCID 5743459Dodecanedial

Conditions

Temperature: -20 °C

Procedure

162.3 g (1 mol) of cyclododecatriene (purity 95%) were dissolved in 1500 ml of methanol, the solution was cooled to -20° C., and an O3 /O2 mixture containing 4% by weight of O3 was passed in until 0.33 mol of ozone had been introduced into the solution. The hydrogenation solution obtained as in Example 1 contained dodecanedial and its acetals. Cyclododecane formed was extracted from the acetic acid solution using petroleum ether prior to the oxidation.

Workup

additionhad been introduced into the solution

Sources & evidence

ORD record: ord-44b3a160828c46d9a7f329c50fde074e
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686638

Reaction notes

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