Cyclohexanone → HCID 12084125, compound

HRID 1266687Notes

Reaction equation

C1(=O)CCCCC1.C#CCCCCCC.[CH:16](/[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C:25]1=[O:30])=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C([O-])(=O)C.[Mn+2].C([O-])(=O)C.C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(O)(=O)C>[CH:16](/[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C:25]1=[O:30])=[CH:17]/[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 20 mmol of cyclohexanone, 2 mmol of 1-octyne, 0.01 mmol of manganese(II) acetate, 0.002 mmol of cobalt (II) acetate and 2 ml of acetic acid was stirred at 50° C. in an atmosphere of air (1 atm=0.101 MPa) for 8 hours. The resulting reaction mixture was analyzed to find that trans-2-(1-octenyl)cyclohexanone and cis-2-(1-octenyl) cyclohexanone were produced in yields of 16% and 13%, respectively, with a conversion from 1-octyne of 45%.

Workup

customThe resulting reaction mixture

Sources & evidence

ORD record: ord-2016f80b1b0a4a32b2edb3fcd653a9cd
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548713B2

Reaction notes

Loading…