Thionyl bromide → 2-Bromo-1,3-dioctadecyloxypropane

HRID 1730824Notes

Reaction equation

HRID 1730824 reaction equation
[CH2:1]([O:19][CH2:20][CH:21](O)[CH2:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].S(Br)([Br:45])=O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:45][CH:21]([CH2:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 68176Thionyl bromideHCID 867912-Propanol, 1,3-bis(octadecyloxy)-HCID 516892Sodium Bicarbonate

Product 1

HCID 214964302-Bromo-1,3-dioctadecyloxypropane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 11.0 g of 1,3-dioctadecyloxy-2-propanol in 400 ml of dry dimethylformamide 20 g of thionyl bromide were added dropwise, while stirring well and boiling, after which the reaction mixture was heated at 100° C for 5 hours. After cooling down said mixture was slowly poured out into 400 ml of 5% sodium bicarbonate solution. The aqueous solution was extracted with 4 × 150 ml of hexane, after which the hexane extract was consecutively washed with water, 5% sodium bicarbonate solution, and water. After drying on sodium sulphate 0 aq the solvent was removed under vacuum. The resulting coarse product was purified by means of column chromatography. After evaporation and drying in vacuum (P = 0.001 mm Hg, t = 40° C) 8 gram were obtained, melting point 47.9° - 48.7° C.

Workup

  1. temperatureAfter cooling down
  2. extractionThe aqueous solution was extracted with 4 × 150 ml of hexane
  3. extractionafter which the hexane extract
  4. washwas consecutively washed with water, 5% sodium bicarbonate solution, and water
  5. dry with materialAfter drying on sodium sulphate 0 aq the solvent
  6. customwas removed under vacuum
  7. customThe resulting coarse product was purified by means of column chromatography
  8. customAfter evaporation
  9. customdrying in vacuum (P = 0.001 mm Hg, t = 40° C) 8 gram
  10. customwere obtained

Sources & evidence

ORD record
ord-bf4e42408f3b48bd97fb2d5c17112282
Source dataset
uspto-grants-1976_11
Patent number
US03993741

Reaction notes

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