1-Bromononane → HCID 86708420, compound

HRID 921482Notes

Reaction equation

HRID 921482 reaction equation
[CH2:1]([CH:3]([CH2:6][CH:7]([CH2:10][CH3:11])[CH2:8][OH:9])[CH2:4][OH:5])[CH3:2].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:12]([O:9][CH2:8][CH:7]([CH2:10][CH3:11])[CH2:6][CH:3]([CH2:1][CH3:2])[CH2:4][OH:5])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 127421-BromononaneHCID 14798Sodium HydroxideHCID 113441631,5-Pentanediol, 2,4-diethyl-

Product 1

HCID 86708420HCID 86708420, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
75 °C

Procedure

Under nitrogen stream, to a 2-L reactor provided with a stirrer, thermometer, condenser and gas inlet tube, 320 g (2 mol) of 2,4-diethyl-1,5-pentanediol, 311 g (1.5 mol) of n-nonylbromide and 12 g of tetrabutylammonium bromide were put, to which 532 g of 52 mass/volume % aqueous sodium hydroxide was added and heated at 70 to 80 degrees C. for six hours with stirring. After the reaction, the mixture was cooled and left still overnight to deposit white crystal. A liquid layer is transferred to a separating funnel by decantation. The white crystal was washed with 20 mL of hexane. The washing liquid of hexane was added to the liquid layer.

Workup

  1. customUnder nitrogen stream, to a 2-L reactor provided with a stirrer
  2. customAfter the reaction
  3. temperaturethe mixture was cooled
  4. waitleft still overnight
  5. customA liquid layer is transferred to a separating funnel by decantation
  6. washThe white crystal was washed with 20 mL of hexane
  7. additionThe washing liquid of hexane was added to the liquid layer

Sources & evidence

ORD record
ord-20608b5d460543e988e64fcf5ed33d3f
Source dataset
uspto-grants-2016_03
Patent number
US09273264B2

Reaction notes

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