1-Pentanol → HCID 59869399, compound
Reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].C([N+](C[CH2:22][CH2:23][CH3:24])(CCCC)CCCC)CCC.[OH-].[Na+].Cl[CH:28]=CC>O>[CH3:28][C:23](=[CH2:22])[CH2:24][O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
In a 3000 mL reaction flask was charged 1-pentanol (400 g, 4.5 mol), a 40% by weight in water solution of tetrabutyl ammonium hydroxide (100 g, 0.15 mol), and a 50% by weight solution of NaOH (435 g, 5.4 mol). The mixture was heated to 70° C. and 3-chloro-2-propene (486 g, 5.4 mol) was fed into the reaction over 3 hours. The reaction was aged for 7 hours at 70° C., then cooled to room temperature. The reaction was quenched with 600 mL of water, and the layers separated. The organic layer washed with 600 mL water and 600 mL of brine. The crude product was purified by distillation to give 435 g of ether, a 68% yield.
Workup
- customIn a 3000 mL reaction flask
- temperaturecooled to room temperature
- customThe reaction was quenched with 600 mL of water
- customthe layers separated
- washThe organic layer washed with 600 mL water and 600 mL of brine
- distillationThe crude product was purified by distillation
- customto give 435 g of ether
Sources & evidence
- ORD record
- ord-3558acbec08d48bd922ab8a351a975d5
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932293B2
Reaction notes
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