Sulfuric Acid → 2-Chloro-5-nitrophenyl 2-hydroxypropyl sulphone

HRID 978638Notes

Reaction equation

HRID 978638 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([O-:13])=[O:12].[Na+].[CH2:15]1[O:18][CH:16]1[CH3:17].S(=O)(=O)(O)O>O>[OH:18][CH:16]([CH3:17])[CH2:15][S:11]([C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6378Propylene OxideHCID 111522Benzenesulfinic acid, 2-chloro-5-nitro-, sodium salt (1:1)

Product 1

HCID 539366392-Chloro-5-nitrophenyl 2-hydroxypropyl sulphone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

150 g (0.5 mol) of 81% pure sodium 2-chloro-5-nitrobenzenesulphinate are presented in 300 ml of water at pH 8-8.5 and 60° C. To this are added dropwise in the couse of about 8 hours 200 ml of propylene oxide while the pH of the reaction mixture is constantly maintained between 7.5 and 9.5 with 20% strength sulphuric acid. After cooling down, the solids are filtered off with suction and washed twice with 200 ml of water. Drying at 70° C. in vacuo gives 118 g of colourless 2-chloro-5-nitrophenyl 2-hydroxypropyl sulphone.

Workup

  1. temperatureAfter cooling down
  2. filtrationthe solids are filtered off with suction
  3. washwashed twice with 200 ml of water
  4. customDrying at 70° C. in vacuo

Sources & evidence

ORD record
ord-1e4083d521fb4911aeffb7239457bffd
Source dataset
uspto-grants-1987_05
Patent number
US04665179

Reaction notes

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