3,3-Dimethyl-1-butene → Methyl Decenoate Neohexene

HRID 1048830

Reaction equation

HRID 1048830 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].[CH3:14][C:15]([CH3:19])([CH3:18])[CH:16]=[CH2:17]>C1(C)C=CC=CC=1>[C:1]([O:12][CH3:13])(=[O:11])[CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:17]=[CH:16][C:15]([CH3:19])([CH3:18])[CH3:14]

Participants

4

Reactant 2

HCID 112103,3-Dimethyl-1-buteneHCID 1778877Methyl 9-decenoate

Product 1

HCID 131735995Methyl Decenoate Neohexene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

10 g of methyl 9-decenoate (54 mmol) purified on alumina, 18.1 g of 3,3-dimethyl-1-butene (neohexene, 215 mmol, 4 equivalents) and 100 g of toluene are placed in a 250 ml 10 glass reactor purged with nitrogen. The mixture is heated at 40° C., followed by addition, over a period of 2 hours, of 3.4 mg of catalyst M73-SiPr supplied by the company Umicore (75 ppm mol) dissolved in 5 ml of toluene. At the end of the addition, the degree of conversion of the methyl decenoate, measured by CPG, is 86%. The selectivity toward cross metathesis product is 35%.

Workup

  1. custompurged with nitrogen
  2. additionfollowed by addition, over a period of 2 hours, of 3.4 mg of catalyst M73-SiPr
  3. dissolutiondissolved in 5 ml of toluene
  4. additionAt the end of the addition

Sources & evidence

ORD record
ord-223caae88ada44d4946ee5d8fb84ba8a
Source dataset
uspto-grants-2016_07
Patent number
US09382189B2

Linked notes

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