Hydroquinone → HCID 57105545, compound

HRID 1196437Notes

Reaction equation

HRID 1196437 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[OH-].[K+].C1(C)C=CC(S(O[CH2:21][CH:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH3:23])(=O)=O)=CC=1>C(O)C>[CH2:25]([O:24][CH:22]([CH3:21])[CH2:23][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 14797Potassium HydroxideHCID 54363232HCID 54363232, compound

Product 1

HCID 57105545HCID 57105545, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.1 g of hydroquinone, 3.1 g of 85% KOH and 100 ml of ethanol were mixed and the reaction was carried out for 2.5 hours. 10.7 g of (2'-dodecyloxypropyl) p-toluenesulfonate was added dropwise and after the reaction was carried out at 60° C. for 3 hours and by heating under reflux for 7.0 hours, ethanol was evaporated. The residue was diluted with 200 ml of water, acidified with a small amount of hydrochloric acid and then extracted with 500 ml of hexane, followed by recrystallization. Yield: 1.1 g (12%). Optical rotation [α]D26° =-8.6°.

Workup

  1. waitafter the reaction was carried out at 60° C. for 3 hours
  2. temperatureby heating
  3. temperatureunder reflux for 7.0 hours
  4. customethanol was evaporated
  5. additionThe residue was diluted with 200 ml of water
  6. extractionextracted with 500 ml of hexane
  7. customfollowed by recrystallization
  8. customOptical rotation [α]D26° =-8.6°

Sources & evidence

ORD record
ord-550d4cc9323e41dfa8bb7120958cac63
Source dataset
uspto-grants-1992_05
Patent number
US05114613

Reaction notes

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