Benzenesulfonyl chloride → 153286-05-6

HRID 1590526Notes

Reaction equation

HRID 1590526 reaction equation
[O:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CCN([CH2:21][CH3:22])CC.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:23]1([S:29]([O:8][C:5]2[CH:6]=[CH:7][C:2]([O:1][C:9]3[CH:14]=[CH:13][C:12]([O:15][S:29]([C:22]4[CH:21]=[CH:25][CH:24]=[CH:23][CH:28]=4)(=[O:31])=[O:30])=[CH:11][CH:10]=3)=[CH:3][CH:4]=2)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 160694,4'-Dihydroxydiphenyl ether

Product 1

HCID 1613853153286-05-6Yield 62%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

An oven-dried 100 ml 3-necked flask is equipped with a magnetic stirring bar, a reflux condenser carrying a CaCl2 -Drierite drying tube, and a heating mantle, and is charged with 4,4'-oxydiphenol (Pfaltz & Bauer (4.2 grams, 20.8 mmol), 4-dimethylaminopyridine (0.5 gram, 4.1 mmol), and anhydrous Et3N (40 ml), and the stirred solution is treated slowly with benzenesulfonyl chloride (6 ml, 47 mmol) via syringe. The resulting mixture is heated at reflux for 9 hours. Workup consists of partitioning the reaction mixture between CH2Cl2 (100 ml) and a mixture of water (150 ml) and concentrated HCl (40 ml), then washing the organic phase successively with 100 ml portions of water, 5 percent NaOH, water, and saturated brine. Drying (MgSO4), filtration and concentration gives a red oily residue. TLC analysis on silica gel shows one major component (Rf =0.36; CH2Cl2), and some minor more polar components. Chromatography on a column packed with flash-grade silica gel (6"×1" i.d.), eluting with CH2Cl2, gives 7.64 grams of a faintly yellowish oil, which solidifies on standing. Recrystallization from a mixture of EtOAc (20 ml) and water (10 ml) affords 6.23 grams (62 percent yield) of the title compound as a white crystalline solid, m.p. 129° C. to 130° C.

Workup

  1. customAn oven-dried 100 ml 3-necked flask is equipped with a magnetic stirring bar, a reflux condenser
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux for 9 hours
  4. customof partitioning the reaction mixture between CH2Cl2 (100 ml)
  5. additiona mixture of water (150 ml) and concentrated HCl (40 ml)
  6. washwashing the organic phase successively with 100 ml portions of water, 5 percent NaOH, water, and saturated brine
  7. customDrying
  8. filtration(MgSO4), filtration and concentration
  9. customgives a red oily residue
  10. washeluting with CH2Cl2
  11. customgives 7.64 grams of a faintly yellowish oil, which
  12. customRecrystallization
  13. additionfrom a mixture of EtOAc (20 ml) and water (10 ml)

Sources & evidence

ORD record
ord-75f3eb5806e64488a8d4c40427eb0758
Source dataset
uspto-grants-1993_04
Patent number
US05204011

Reaction notes

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