Hydroquinone → HCID 86740095, compound

HRID 462809Notes

Reaction equation

HRID 462809 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:21]1([CH:28]=[CH:27][C:25]([OH:26])=[CH:24][CH:23]=1)[OH:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:21]1([CH:28]=[CH:27][C:25]([OH:26])=[CH:24][CH:23]=1)[OH:22]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 6101p-Toluenesulfonic acidHCID 445639Oleic Acid

Product 1

HCID 86740095HCID 86740095, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 28.2 gm (0.101 mole) oleic acid in toluene, was added 12 gm hydroquinone (0.11 mole) and 1.7 gm p-toluenesulfonic acid (0.01 mole). Water was withdrawn into a Dean-Stark trap as the solvent was refluxed for two days. The solution was cooled and washed with 100 ml water four times, and the solvent was evaporated in vacuo. The crystalline residue was recrystallized from methanol to give 15 gm hydroquinone oleate (40% theoretical) colorless compound, single spot (TLC). The melting point was 85° C. and the NMR was consistent with the structure of hydroquinone oleate.

Workup

  1. customWater was withdrawn into a Dean-Stark trap as the solvent
  2. temperaturewas refluxed for two days
  3. temperatureThe solution was cooled
  4. washwashed with 100 ml water four times
  5. customthe solvent was evaporated in vacuo
  6. customThe crystalline residue was recrystallized from methanol

Sources & evidence

ORD record
ord-e7667ef198ff45e392617674ca4a423e
Source dataset
uspto-grants-1985_05
Patent number
US04517347

Reaction notes

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