p-Toluenesulfonic acid → HCID 18979162, compound

HRID 2393177Notes

Reaction equation

HRID 2393177 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([OH:12])=[CH:8][CH:9]=[C:10]([OH:11])[C:4]2=[CH:3][CH:2]=1.O[CH:14]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH:14]([C:9]2[C:10](=[O:11])[C:4]3[C:5]([C:7](=[O:12])[CH:8]=2)=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 113051,4-NaphthalenediolHCID 18979260HCID 18979260, compound

Product 1

HCID 18979162HCID 18979162, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,4-Naphthohydroquinone (8 g) was reacted with 6-hydroxy-6-(4-methoxyphenyl)hexanoic acid (11.9 g) in the presence of p-toluenesulfonic acid (3.8 g) in toluene (200 ml) at 80° C. for 15 hours. Then, the reaction mixture was extracted with ethyl acetate and concentrated. The residue was submitted to an overnight reaction with an aqueous solution (120 ml) of iron (III) chloride hexahydrate (31 g) (0.1 ml) in acetic acid (70 ml) at room temperature. This reaction mixture was extracted with ethyl acetate and concentrated and the residue was purified by silica gel column chromatography. Recrystallization from hexane-ethyl acetate gave 4 g of the title compound.

Workup

  1. extractionThen, the reaction mixture was extracted with ethyl acetate
  2. concentrationconcentrated
  3. customreaction with an aqueous solution (120 ml) of iron (III) chloride hexahydrate (31 g) (0.1 ml) in acetic acid (70 ml) at room temperature
  4. extractionThis reaction mixture was extracted with ethyl acetate
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel column chromatography
  7. customRecrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-8f4a210ba37744c28174331a465d8fb3
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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