Benzene → HCID 19806990, compound

HRID 1681104Notes

Reaction equation

HRID 1681104 reaction equation
[C:1]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=[C:7]([CH3:16])[C:6]=1[N:17]([CH3:19])[CH3:18])([CH3:4])([CH3:3])[CH3:2].[B:20](O)([OH:22])[OH:21].C1C=CC=CC=1>O>[B:20]([O:11][C:10]1[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[C:6]([N:17]([CH3:19])[CH3:18])[C:7]([CH3:16])=[CH:8][C:9]=1[C:12]([CH3:13])([CH3:15])[CH3:14])([OH:22])[OH:21]

Participants

5

Reactant 3

HCID 241BenzeneHCID 7628Boric AcidHCID 30157193-(Dimethylamino)-2,6-bis(1,1-dimethylethyl)-p-cresol

Product 1

HCID 19806990HCID 19806990, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2,6-di-tertiary-butyl-dimethylamino- p-cresol (131.5 gm, 0.5 mole), boric acid (31.0 gm, 0.5 mole), and benzene (450 ml.) was heated while stirring vigorously at 85° C. for twenty-two hours. Water (5.5 ml.) formed during reaction was collected by azeotropic distillation.At the end of the reaction, the unreacted, insoluble material was removed by filtration, and the benzene was removed under reduced pressure using a rotary evaporator. This gave a golden orange solid (129.5 gm) with a melting point of 75°-80° C.

Workup

  1. temperaturewas heated
  2. distillationwas collected by azeotropic distillation.At
  3. customthe end of the reaction
  4. customthe unreacted, insoluble material was removed by filtration
  5. customthe benzene was removed under reduced pressure
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-9fbdf83805c645839207f74b251ee571
Source dataset
uspto-grants-1992_12
Patent number
US05169547

Reaction notes

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