Trimethylolpropane → HCID 86708418, compound

HRID 921480Notes

Reaction equation

HRID 921480 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].[CH2:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:10]([O:2][CH2:1][C:3]([CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([CH2:4][CH3:5])[CH2:6][OH:7])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6510TrimethylolpropaneHCID 127421-BromononaneHCID 14798Sodium Hydroxide

Product 1

HCID 86708418HCID 86708418, 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, 107.3 g (0.8 mol) of trimethylolpropane and 249 g (1.2 mol) of n-nonyl bromide and 11.4 g of tetrabutyl ammonium bromide were put, to which 360 g of 50 mass/volume % aqueous sodium hydroxide was added and heated at 70 to 80 degrees C. for four 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. An alkali layer of an under layer was removed by separation. An organic layer was washed with 400 mL of saturated saline and 50 mL of a dilute aqueous solution of sulfuric acid. After the organic layer was further washed with distilled water until becoming neutral, 190 g of the obtained organic layer was dried with magnesium sulfate.

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. customAn alkali layer of an under layer was removed by separation
  7. washAn organic layer was washed with 400 mL of saturated saline and 50 mL of a dilute aqueous solution of sulfuric acid
  8. washAfter the organic layer was further washed with distilled water
  9. dry with material190 g of the obtained organic layer was dried with magnesium sulfate

Sources & evidence

ORD record
ord-80a42cb71b1a418fb8dde8eaded63734
Source dataset
uspto-grants-2016_03
Patent number
US09273264B2

Reaction notes

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