Sulfuric Acid → HCID 12087647, compound

HRID 396595Notes

Reaction equation

HRID 396595 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=O)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>[Zn]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([SH:15])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chloride

Product 1

HCID 12087647HCID 12087647, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Zinc dust (13.1 g) was added to a mixture of 4-Benzyloxy-benzenesulfonyl chloride (I) (10 g, 35.2 mmoles), sulfuric acid (26.2 g) and ice (78.6 g) at 0° C. The mixture was warmed to ambient temperature, stirred for 1 hour, refluxed for 2 hours and then cooled to ambient temperature. The mixture was extracted twice with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound. 1H NMR (CDCl3, 400 MHz) δ 5.03 (s, 2H), 6.89 (d, J=8.92 Hz, 2H), 7.38 (d, J=8.93 Hz, 2H), 7.3-7.4 (m, 5H).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturecooled to ambient temperature
  3. extractionThe mixture was extracted twice with ethyl acetate
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49cf31ee6d7e431eb19035bd5e0666df
Source dataset
uspto-grants-2003_08
Patent number
US06608104B2

Reaction notes

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