Methyl formate → Methyl cyclohexanecarboxylate

HRID 929406Notes

Reaction equation

HRID 929406 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH:7]([O:9][CH3:10])=[O:8]>[Ru].[Co]>[CH:1]1([C:7]([O:9][CH3:10])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Conditions

Temperature
120 °C

Procedure

In a pressure reactor made of stainless steel and having an internal volume of 50 ml, 0.05 mmol of [Ru(CO)3Cl2]2 as a ruthenium compound, 0.05 mmol of Co2(CO)8 as a cobalt compound, and 1.0 mmol of [bis(triphenylphosphine)iminium]iodide as a halide salt were introduced and mixed at room temperature, and thus a catalyst system was obtained. 5.0 mmol of cyclohexene and 5.0 mL of methyl formate were added to this catalyst system, subsequently the reactor was purged with nitrogen gas at 0.5 MPa, and the system was maintained for 15 hours at 120° C. Thereafter, the reactor was cooled to room temperature, and the pressure was released. A portion of the remaining organic phase was withdrawn, and the components of the reaction mixture were analyzed by using gas chromatography. According to the analysis results, the amount of methyl cyclohexanecarboxylate produced by the reaction was 2.47 mmol (yield in terms of cyclohexene 49.4%).

Workup

  1. additionwere introduced
  2. additionmixed at room temperature
  3. customthus a catalyst system was obtained
  4. customsubsequently the reactor was purged with nitrogen gas at 0.5 MPa
  5. temperatureThereafter, the reactor was cooled to room temperature
  6. customA portion of the remaining organic phase was withdrawn
  7. customresults

Sources & evidence

ORD record
ord-cbd7dcc5ee724b53a99b667536bfdee7
Source dataset
uspto-grants-2016_03
Patent number
US09295981B2

Reaction notes

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