Toluene → Ethyl 5-methyl-2-(prop-1-en-2-yl)hex-4-enoate
Reaction equation
[C:1]([CH:4]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[C:5]([OH:7])=[O:6])([CH3:3])=[CH2:2].C(=O)([O-])[O-].[K+].[K+].[C:19]1(C)C=CC=C[CH:20]=1.S(OCC)(OCC)(=O)=O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([CH:4]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[C:5]([O:7][CH2:19][CH3:20])=[O:6])([CH3:3])=[CH2:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
In a nitrogen atmosphere, a mixture of 200.01 g of 2-isopropenyl-5-methyl-4-hexenoic acid (1) having a purity of 85.4%, 89.82 g of potassium carbonate, 11.28 g of tetrabutylammonium chloride, and 800 g of toluene was heated to from 95° C. to 100° C., while being stirred, and then 191.8 g of diethyl sulfate was added dropwise thereto over 35 minutes. The reaction mixture was heated continuously for 2 hours, then cooled to room temperature, and subjected to addition of 510 g of water. The toluene solution was separated from the resulting mixture and then subjected to typical work-up including washing, drying and concentration to obtain the crude product. The crude product was distilled under reduced pressure to obtain 193.4 g of the intended product having a purity of 99.7%. The yield was 97%.
Workup
- temperaturewas heated to from 95° C. to 100° C.
- temperatureThe reaction mixture was heated continuously for 2 hours
- customThe toluene solution was separated from the resulting mixture
- washincluding washing
- customdrying
- concentrationconcentration
- customto obtain the crude product
- distillationThe crude product was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-c7ac0fb1b4434935b23c2c3d91fab189
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126923B2
Reaction notes
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