Catechol → HCID 67706108, compound

HRID 1451993Notes

Reaction equation

HRID 1451993 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([NH2:12])[C:6]=1[NH2:13])([CH3:4])([CH3:3])[CH3:2].[C:14]1([CH:21]=[CH:20][C:18]([OH:19])=[CH:17][CH:16]=1)[OH:15].C1(C(=CC=CC=1)O)O.O=O.[OH-].[Na+]>C(OCCO)CC.OO.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].C(O)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([NH2:12])[C:6]=1[NH2:13])([CH3:4])([CH3:2])[CH3:3].[C:18]1(=[O:19])[CH:20]=[CH:21][C:14](=[O:15])[CH:16]=[CH:17]1

Participants

11

Reactant 5

HCID 289CatecholHCID 785HydroquinoneHCID 977OxygenHCID 14798Sodium HydroxideHCID 20139668HCID 20139668, compound

Product 1

HCID 67706108HCID 67706108, compound

Reagents, catalysts & solvents 5

HCID 784Hydrogen PeroxideCatalystHCID 24463Copper sulfate pentahydrateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 17756Glycol monopropyl etherSolvent

Procedure

About 3.56 g (0.02 mol) t-butyltoluenediamine was dissolved in about 30 mL ethyleneglycol monopropyl ether. About 2.4 mL glacial acetic acid was added followed by about 1.98 g (0.018 mol) hydroquinone, about 0.22 g (0.002 mol) catechol (chemical name 1,2-dihydroxybenzene), and about 0.2 g copper sulfate pentahydrate. About 10 drops of 1% hydrogen peroxide was added and oxygen was passed for about 5 hours, at a rate of about 40 cc/min. When the reaction was over, about 1.7 g sodium hydroxide, dissolved in about 3 mL of water was added and the mixture was stirred for about 15 min. Reaction product is obtained by pouring the reaction mixture into water and filtering the precipitated polymer and drying it in vacuo.

Workup

  1. additionwas added
  2. customReaction product
  3. customis obtained
  4. filtrationfiltering the precipitated polymer
  5. customdrying it in vacuo

Sources & evidence

ORD record
ord-80c8709a02fc4f4ab5b19cc8360455d5
Source dataset
uspto-grants-1997_02
Patent number
US05606010

Reaction notes

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