1-Hexanol → HCID 17792285, compound

HRID 2079929Notes

Reaction equation

HRID 2079929 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].C([N+](C[CH2:23][CH2:24][CH3:25])(CCCC)CCCC)CCC.[OH-].[Na+].Cl[CH:29]=CC>O>[CH3:29][C:24](=[CH2:23])[CH2:25][O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 81031-HexanolHCID 115361-ChloropropeneHCID 14798Sodium HydroxideHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 17792285HCID 17792285, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

In a 3000 mL reaction flask was charged 1-hexanol (500 g, 4.9 mol), a 40% by weight in water solution of tetrabutyl ammonium hydroxide (65 g, 0.10 mol), and a 50% by weight solution of NaOH (480 g, 6.6 mol). The mixture was heated to 70° C. and 3-chloro-2-propene (530 g, 5.9 mol) was fed into the reaction over 3 hours. The reaction was aged for 7 hours at 70° C., and then cooled to room temperature. The reaction was quenched with 800 mL of water, and the layers separated. The organic layer washed with 800 mL water and 800 mL of brine. The crude product was purified by distillation to give 550 g of ether, a 72% yield.

Workup

  1. customIn a 3000 mL reaction flask
  2. temperaturecooled to room temperature
  3. customThe reaction was quenched with 800 mL of water
  4. customthe layers separated
  5. washThe organic layer washed with 800 mL water and 800 mL of brine
  6. distillationThe crude product was purified by distillation
  7. customto give 550 g of ether

Sources & evidence

ORD record
ord-bc599c1fe2944c2eb24ad67787f93576
Source dataset
uspto-grants-2011_04
Patent number
US07932293B2

Reaction notes

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