HCID 13781841, compound → HCID 14121496, compound

HRID 648430Notes

Reaction equation

HRID 648430 reaction equation
[C:1]1([CH3:32])[CH:6]=[CH:5][C:4]([S:7]([C:10]2[C:22]([OH:23])=[C:21]([C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25])[CH:20]=[C:19]([OH:31])[C:11]=2[C:12]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1>[O-2].[O-2].[Mn+4].C1C=CC=CC=1>[C:1]1([CH3:32])[CH:2]=[CH:3][C:4]([S:7]([C:10]2[C:22](=[O:23])[C:21]([C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25])=[CH:20][C:19](=[O:31])[C:11]=2[C:12]([O:14][CH2:15][CH:16]([CH3:17])[CH3:18])=[O:13])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 13781841HCID 13781841, compound

Product 1

HCID 14121496HCID 14121496, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

One part of diisobutyl 2-p-toluenesulfonyl-3,6dihydroxyterephthalate, 3 parts of electrolytic manganese dioxide and 5 parts of benzene were mixed. After allowing the mixture to stand for 24 hours, it was agitated at its boiling point for 3 hours. The reaction mixture was hot-filtered, and a portion of the benzene was distilled off to concentrate the filtrate to about 1/3 of its initial volume. Upon addition of ligroin, a yellowish precipitate was caused to deposit. The mixture was allowed to cool overnight at room temperature and the solid matter was collected by filtration. Then, it was washed with ligroin and dried at room temperature in air, thereby obtaining light-yellowish crystals having a melting point of 112°-114° C. with a yield of about 70%.

Workup

  1. filtrationThe reaction mixture was hot-filtered
  2. distillationa portion of the benzene was distilled off
  3. concentrationto concentrate the filtrate to about 1/3 of its initial volume
  4. additionUpon addition of ligroin
  5. filtrationthe solid matter was collected by filtration
  6. washThen, it was washed with ligroin
  7. customdried at room temperature in air

Sources & evidence

ORD record
ord-94dd195dc81544e99168805b4c68d81f
Source dataset
uspto-grants-1988_04
Patent number
US04735744

Reaction notes

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