Water → 4-(2,3-Pentadienyloxy)benzenesulfonyl Chloride

HRID 1180540Notes

Reaction equation

HRID 1180540 reaction equation
[Na+].[CH2:2]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O-:17])(=O)=[O:15])=[CH:10][CH:9]=1)[CH:3]=[C:4]=[CH:5][CH3:6].P(Cl)(Cl)([Cl:20])=O.O>C(#N)C.S1(CCCC1)(=O)=O>[CH2:2]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([Cl:20])(=[O:17])=[O:15])=[CH:10][CH:9]=1)[CH:3]=[C:4]=[CH:5][CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 589789204-(2,3-Pentadienyloxy)benzenesulfonic acid sodium salt

Product 1

HCID 858262484-(2,3-Pentadienyloxy)benzenesulfonyl ChlorideYield 65%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
62.5 °C

Procedure

To a suspension of product from Example 9 (740 mg, 2.48 mmol) in acetonitrile (2 ml) and sulfolane (2 ml) was added phosphoryl chloride (0.9 ml, 9.93 mmol) and the resulting mixture was heated at 60-65° C. for 2 hours. The mixture was cooled in ice and cold water was added, dropwise, while stirring was continued for an additional 15 minutes. The reaction mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous sodium sulfate. The crude residue was purified by flash chomatography to give 415 mg (65%) of the product.

Workup

  1. temperatureThe mixture was cooled in ice
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customThe crude residue was purified by flash chomatography

Sources & evidence

ORD record
ord-947ebdadbf294031b895a0cedabb3092
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

Loading…