Water → HCID 19832966, compound

HRID 2051160Notes

Reaction equation

HRID 2051160 reaction equation
[C:1]([O:4][C:5]1[C:14]([O:15][C:16](=[O:18])[CH3:17])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:19]([OH:22])(=O)=[O:20])[CH:11]=2)[CH:6]=1)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:24].O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[C:14]([O:15][C:16](=[O:18])[CH3:17])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:19]([Cl:24])(=[O:22])=[O:20])[CH:11]=2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24819Phosphorus pentachlorideHCID 19832978HCID 19832978, compound

Product 1

HCID 19832966HCID 19832966, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of the crude 2,3-diacetoxy-6-naphthalenesulphonic acid (973 mg) in CCl4 (3 ml) was added phosphorus pentachloride (750 mg). The mixture was heated at 80° C. for 20 minutes, cooled, and water added cautiously. The CCl4 was separated from the aqueous layer and the latter was extracted with CH2Cl2. The organic extracts were combined, washed with water and dried over magnesium sulphate. Evaporation of the solvent yielded 2,3-diacetoxy-6-naphthalenesulphonyl chloride (160 mg, yield: 15%). NMR in CDCl3 : 2.37(s,6H); 7.82(s,1H); 7.87(s,1H); 7.99(s,1H); 8.01(s,1H); 8.54(br.s,1H).

Workup

  1. temperaturecooled
  2. customThe CCl4 was separated from the aqueous layer
  3. extractionthe latter was extracted with CH2Cl2
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ff946e60bd73417399bf8cc9c3f1b304
Source dataset
uspto-grants-1991_05
Patent number
US05017569

Reaction notes

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