Hydroquinone → HCID 57162460, compound

HRID 1638958Notes

Reaction equation

HRID 1638958 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[OH-].[K+].O.C1(C)C=CC(S(O[CH2:22][CH:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH3:24])(=O)=O)=CC=1>C(O)C>[CH2:26]([O:25][CH:23]([CH3:22])[CH2:24][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 962WaterHCID 14797Potassium HydroxideHCID 19880015HCID 19880015, compound

Product 1

HCID 57162460HCID 57162460, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17.0 g of hydroquinone, 11.4 g of 85% KOH, 7.5 ml of water and 200 ml of ethanol were added into a four-necked flask, and after the reaction for 5 hours, the mixture was elevated in temperature to 50° C. and 33 g of (2'-octyloxypropyl) p-toluenesulfonate was added dropwise thereto. After the reaction for 5 hours, the mixture was heated at reflux for 11 hours and thereafter ethanol was evaporated. The residue was added into 600 ml of water and acidified with hydrochloric acid. The mixture was extracted with 500 ml of hexane and the extract was dried over anhydrous Na2SO4, followed by recrystallization. Yield: 4.2 g (16%). Optical rotation [α]D26.2° =-11.3°.

Workup

  1. customafter the reaction for 5 hours
  2. customwas elevated in temperature to 50° C.
  3. customAfter the reaction for 5 hours
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 11 hours
  6. customethanol was evaporated
  7. additionThe residue was added into 600 ml of water
  8. extractionThe mixture was extracted with 500 ml of hexane
  9. dry with materialthe extract was dried over anhydrous Na2SO4
  10. customfollowed by recrystallization
  11. customOptical rotation [α]D26.2° =-11.3°

Sources & evidence

ORD record
ord-08d1baa79fc842f1bc0bafe0965993de
Source dataset
uspto-grants-1989_11
Patent number
US04882085

Reaction notes

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