Hydrochloric Acid → 2,4-dihydroxybenzenesulfonic Acid

HRID 586777Notes

Reaction equation

HRID 586777 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].C(=O)(OC)OC.Cl.Cl[S:17]([OH:20])(=[O:19])=[O:18]>C1CCCCC1>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[S:17]([OH:20])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 5054ResorcinolHCID 12021Dimethyl CarbonateHCID 24638Chlorosulfonic acid

Product 1

HCID 53121172,4-dihydroxybenzenesulfonic Acid

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
60 °C

Procedure

15.0 g (0.136 moles) of resorcinol, 102 g dimethyl carbonate and 68 g cyclohexane were charged under nitrogen to a 4-necked one litre reactor fitted with stirrer, thermometer and condenser attached to an HCl scrubber system. The reaction mixture was heated to 60° C. and 15.1 g (0.13 moles) of chlorosulphonic acid added over a period of 4 h with removal of hydrogen chloride gas. On completion of the addition, the reaction mixture is heated to 70-72° C. for 1 h, and then cooled to 20° C. The reaction mixture separated into two layers with the lower layer containing 2,4-dihydroxybenzene sulphonic Acid (63.2% by hplc) and resorcinol (31.5% by hplc).

Workup

  1. customfitted with stirrer
  2. additionOn completion of the addition
  3. temperaturethe reaction mixture is heated to 70-72° C. for 1 h
  4. temperaturecooled to 20° C
  5. customThe reaction mixture separated into two layers with the lower layer
  6. additioncontaining 2,4-dihydroxybenzene sulphonic Acid (63.2% by hplc) and resorcinol (31.5% by hplc)

Sources & evidence

ORD record
ord-2d3f717750df45f99564e4817d8166d0
Source dataset
uspto-grants-2005_08
Patent number
US06936732B2

Reaction notes

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