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

HRID 1730823Notes

Reaction equation

HRID 1730823 reaction equation
[CH2:1]([O:19][CH2:20][C:21]([O: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][CH2:41][CH3:42])(O)[CH3:22])[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.[Na].C(=O)(O)[O-]>CN(C)C=O>[Br:45][CH2:22][CH:21]([O: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][CH2:41][CH3:42])[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 214964311,2-Dioctadecyloxy-2-propanolHCID 50987224Sodium hydrogen-carbonate

Product 1

HCID 203572611-Bromo-2,3-dioctadecyloxypropane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 15 g of 1,2-dioctadecyloxy-2-propanol in 450 ml of dimethylformamide 21 g of thionylbromide were added dropwise while stirring and cooling, after which the reaction mixture was heated at 100° C for 5 hours. After cooling down, the resultant mixture was slowly poured into 400 ml of 5% sodium-bicarbonate solution. The aqueous solution was extracted with 4 × 150 ml of diethylether, after which the ether extract was consecutively washed with water, 5% sodium bicarbonate solution and water. After drying on sodium sulphate the solvent was removed under vacuum. The coarse product thus obtained was purified by means of column chromatography. The yield was 14 g of 1-bromo-2,3-dioctadecyloxypropane with a melting point of 38°-38.8° C.

Workup

  1. temperaturecooling
  2. temperatureAfter cooling down
  3. extractionThe aqueous solution was extracted with 4 × 150 ml of diethylether
  4. extractionafter which the ether extract
  5. washwas consecutively washed with water, 5% sodium bicarbonate solution and water
  6. customAfter drying on sodium sulphate the solvent
  7. customwas removed under vacuum

Sources & evidence

ORD record
ord-8e114bea551a4c748c524a280b96a4e4
Source dataset
uspto-grants-1976_11
Patent number
US03993741

Reaction notes

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