Bis(dichloromethyl) ether → alpha-Sulfo-3-(chloromethyl)-4-hydroxybenzeneacetic acid

HRID 2049212Notes

Reaction equation

HRID 2049212 reaction equation
[S:1]([CH:5]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:6]([OH:8])=[O:7])([OH:4])(=[O:3])=[O:2].[Cl:16][CH:17](OC(Cl)Cl)Cl>S(=O)(=O)(O)O>[S:1]([CH:5]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:17][Cl:16])[CH:10]=1)[C:6]([OH:8])=[O:7])([OH:4])(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 558102Bis(dichloromethyl) etherHCID 3373694(4-Hydroxy-phenyl)-sulfo-acetic acid

Product 1

HCID 20296128alpha-Sulfo-3-(chloromethyl)-4-hydroxybenzeneacetic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

α-Sulfo-4-hydroxybenzeneacetic acid, 0.3 mole, is dissolved in aqueous sulfuric acid (50%). One equivalent of dichloromethyl ether is added to the solution maintained at between 35° to 45° C. Hydrogen chloride is then bubbled through this reaction mixture for 3 hours. The desired compound is recovered by pouring the reaction mixture into water and extracting the title compound with ethyl acetate. The ethyl acetate is dried over magnesium sulfate. The magnesium sulfate is removed by filtration and evaporation of the ethyl acetate gives the desired compound.

Workup

  1. temperaturemaintained at between 35° to 45° C
  2. customHydrogen chloride is then bubbled through this reaction mixture for 3 hours
  3. customThe desired compound is recovered
  4. additionby pouring the reaction mixture into water
  5. extractionextracting the title compound with ethyl acetate
  6. dry with materialThe ethyl acetate is dried over magnesium sulfate
  7. customThe magnesium sulfate is removed by filtration and evaporation of the ethyl acetate

Sources & evidence

ORD record
ord-880fdde6fce944ba898a8dc841a34523
Source dataset
uspto-grants-1980_04
Patent number
US04197240

Reaction notes

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