Hydroquinone → HCID 57105545, compound

HRID 1638962Notes

Reaction equation

HRID 1638962 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-898720c4ddc84a0dae48807658b9a461
Source dataset
uspto-grants-1989_11
Patent number
US04882085

Reaction notes

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