Hydrochloric Acid → HCID 86597002, compound

HRID 586778Notes

Reaction equation

HRID 586778 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][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([S:17]([OH:20])(=[O:19])=[O:18])[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 785HydroquinoneHCID 12021Dimethyl CarbonateHCID 24638Chlorosulfonic acid

Product 1

HCID 86597002HCID 86597002, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
60 °C

Procedure

15.0 g (0.136 moles) of hydroquinone, 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 1,4-dihydroxybenzene sulphonic acid (60% by hplc) and hydroquinone (38% 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 1,4-dihydroxybenzene sulphonic acid (60% by hplc) and hydroquinone (38% by hplc)

Sources & evidence

ORD record
ord-674749ae87c94684bd323970c15bcca1
Source dataset
uspto-grants-2005_08
Patent number
US06936732B2

Reaction notes

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