Acetyl chloride → HCID 22621687, compound
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH2:11][CH:10]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>CCOCC>[C:19]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH2:11][CH:10]=1)(=[O:21])[CH3:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A solution of 2.5 mmol of 1-(7-hydroxyheptyl)-cyclopropene in 5 ml of ether was cooled in an ice bath. Triethylamine (0.44 ml) and 0.21 g (2.7 mmol) of acetyl chloride were added, and the reaction mixture was stirred 1 hour at 5° C. Additional acetyl chloride (0.11 g), ether and triethylamine were added, and the reaction was stirred at 5° C. until GC analysis indicated 95% conversion. The reaction was worked up by adding more ether and washing the organic phase with water, dilute HCl solution (diluted 1M aqueous HCl), potassium carbonate solution (2×), water and brine. The ether phase was dried over magnesium sulfate and stripped. Hexane was added and the reaction was stripped again to give 1-(7-acetoxyheptyl)-cyclopropene.
Workup
- stirringthe reaction was stirred at 5° C. until GC analysis
- washwashing the organic phase with water, dilute HCl solution (diluted 1M aqueous HCl), potassium carbonate solution (2×), water and brine
- dry with materialThe ether phase was dried over magnesium sulfate
- additionHexane was added
Sources & evidence
- ORD record
- ord-d93ab076a862401a82db41216f5fd186
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06365549B2
Reaction notes
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