Sulfuryl chloride → 2-Chloro-5-(hexadecan-2-yl)benzene-1,4-diol

HRID 1589774Notes

Reaction equation

HRID 1589774 reaction equation
[CH:1]([C:17]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:18]=1[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][CH3:16])[CH3:2].S(Cl)([Cl:28])(=O)=O>C(Cl)Cl>[Cl:28][C:21]1[CH:20]=[C:18]([OH:19])[C:17]([CH:1]([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][CH3:16])[CH3:2])=[CH:23][C:22]=1[OH:24]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 15131569HCID 15131569, compound

Product 1

HCID 150348942-Chloro-5-(hexadecan-2-yl)benzene-1,4-diolYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

33.5 g (0.1 mol)of 2-sec-hexadecylhydroquinone was dissolved in 300 ml of methylene chloride and to a resulting solution was added dropwise 8.1 ml (0.1 mol) of sulfuryl chloride with stirring at room temperature over a period of 30 minutes. After stirring for 6 hours at room temperature, the reaction mixture was allowed to stand overnight and extracted with ethyl acetate. The extract was washed three times with a 5% aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography (solvent: chloroform) to obtain 27 g of the desired 2-chloro-5-sec-hexadecylhydroquinone as the light from oily product. The structure thereof was confirmed by NMR and mass spectra.

Workup

  1. stirringAfter stirring for 6 hours at room temperature
  2. waitto stand overnight
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed three times with a 5% aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (solvent: chloroform)

Sources & evidence

ORD record
ord-b530a524aa914f44939eee9ce1cdd882
Source dataset
uspto-grants-1993_04
Patent number
US05200304

Reaction notes

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