Water → HCID 10861038, compound

HRID 1906051Notes

Reaction equation

HRID 1906051 reaction equation
[CH2:1]=[CH: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].[OH2:19].[Br:20]N1C(=O)CCC1=O>CS(C)=O>[Br:20][CH2:1][CH:2]([OH:19])[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].[Br:20][CH: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])[CH2:1][OH:19]

Participants

6

Reactant 3

HCID 962Water2×HCID 82171-OctadeceneHCID 67184N-bromobutanimide

Product 2

HCID 10861038HCID 10861038, compoundHCID 10959015HCID 10959015, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

While stirring vigorously 15.12 g (60 mmoles) of 1-octadecene in 300 ml of DMSO containing 2.7 g of water, 21.36 g (120 mmoles) of N-bromosuccinimide was added over a period of 40 minutes. The mixture was stirred at room temperature for 100 minutes, poured into a cold water and extracted with ether. The extract was washed with water, dried and concentrated. The residue was purified by recrystallization and silica gel chromatography to give 10.7 g of 1-bromo-2-hydroxyoctadecane (m.p. 53.5°-54.5° C.), 3.0 g of 2-bromo-1-octadecanol (m.p. 39°-39.5° C.) and 3.78 g of a mixture of these compounds.

Workup

  1. additionwas added over a period of 40 minutes
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by recrystallization and silica gel chromatography

Sources & evidence

ORD record
ord-a5ba8b15d8134d728f9700fc66fa412f
Source dataset
uspto-grants-1987_03
Patent number
US04649203

Reaction notes

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