Methyl 5-chloro-2,2-dimethylvalerate synthesis
- Product Name:Methyl 5-chloro-2,2-dimethylvalerate
- CAS Number:73441-42-6
- Molecular formula:C8H15ClO2
- Molecular Weight:178.66
100-42-5
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$23.00/25mL
547-63-7
235 suppliers
$13.00/5g
109-70-6
494 suppliers
$10.00/5g
73441-42-6
39 suppliers
$284.00/1g
Yield:73441-42-6 107.7 g (74%)
Reaction Conditions:
with diisopropylamine in tetrahydrofuran;hexane;water;
Steps:
1 Preparation of Methyl 5-Chloro-2,2-dimethylpentanoate
EXAMPLE 1 Preparation of Methyl 5-Chloro-2,2-dimethylpentanoate Lithium metal shot (6.31 g, 0.91 mol) was weighed under an argon atmosphere and placed in an argon-filled 1-liter flask. Tetrahydrofuran (182 ml) and diisopropylamine (96.6 g, 0.955 mol) were added. The mixture was heated to 35° C. while styrene (48.8 g, 0.468 mol) was added slowly while maintaining the temperature between 35° C. and 42° C. When the addition of styrene was complete, and the exotherm had subsided, the mixture was cooled and methyl isobutyrate (83.6 g, 0.819 mol) was added dropwise at 5° C. to 10° C. Next, 1-bromo-3-chloropropane (193.7 g, 1.23 mol) was added at temperatures between 10° C. and 35° C. (mainly below 15° C.) and the mixture was allowed to warm to room temperature over a period of three days. The reaction mixture was then quenched by the addition of 40 ml of water, and the volume of the solution was reduced to 200 ml under vacuum. This residue was partitioned between 200 ml of hexane and 200 ml of water. The layers separated, and the aqueous layer was washed weith 100 ml of hexane. The combined organic layers were distilled and the product fraction collected at 56° C. to 62° C. (4 torr, 0.52 kPascal) to yield 107.7 g (74%) of methyl 5-chloro-2,2-dimethylpentanoate.
References:
US4665226,1987,A
6940-76-7
173 suppliers
$6.00/1g
547-63-7
235 suppliers
$13.00/5g
73441-42-6
39 suppliers
$284.00/1g
547-63-7
235 suppliers
$13.00/5g
109-70-6
494 suppliers
$10.00/5g
73441-42-6
39 suppliers
$284.00/1g