Water → Oleylphenylsulfone

HRID 436936Notes

Reaction equation

HRID 436936 reaction equation
[C:1]1([S:7]([CH:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])CCCCC)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Br)CCCCCCC/C=C\CCCCCCCC.C1(S([O-])=O)C=CC=CC=1.[Na+].O>CN(C)C=O>[CH2:10]([S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 2723840Benzenesulfinic acid, sodium saltHCID 58403839-Octadecene, 1-bromo-, (9Z)-HCID 146818286-Phenylsulfonyl-cis-tricos-14-ene

Product 1

HCID 14681826OleylphenylsulfoneYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

The initial oleylphenylsulfone may be prepared in the following manner: a mixture of 16.5 g (5.10-2 mole) oleyl bromide and 8.2 g (5.10-2 mole) sodium phenyl sulphinate in 100 cm3 dimethylformamide is stirred for 15 hours at 25° C. The reaction mixture is then poured into 800 cm3 iced water and the organic phase is extracted five times with ether. The combined ethereal extracts are washed with a saturated aqueous solution of sodium chloride then dried over magnesium sulphate and concentrated. The residue obtained is purified by being passed over a silica column (elution solvent: cyclohexane). By concentration of the eluate, 15 g (yield: 77%) oleylphenylsulfone are obtained in the form of a colourless oil identified by NMR and infrared spectrography.

Workup

  1. extractionthe organic phase is extracted five times with ether
  2. washThe combined ethereal extracts are washed with a saturated aqueous solution of sodium chloride
  3. dry with materialthen dried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customis purified
  7. washby being passed over a silica column (elution solvent: cyclohexane)

Sources & evidence

ORD record
ord-1423c557dddc4c9a97a9aa0e57bb82cb
Source dataset
uspto-grants-1977_06
Patent number
US04028422

Reaction notes

Loading…