Boron trifluoride etherate → HCID 15599098, compound

HRID 986804Notes

Reaction equation

HRID 986804 reaction equation
[C:1]([C:5]1[C:10](=[O:11])[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:7](=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23])[CH3:18].B(F)(F)F.CCOCC>O1CCCC1>[C:1]([C:5]1[C:10](=[O:11])[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:7](=[N:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:20]([O:19][CH2:17][CH3:18])[CH:21]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 121203-EthoxyanilineHCID 128672,6-Di-t-butyl-p-benzoquinone

Product 1

HCID 15599098HCID 15599098, compoundYield 2.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 22.0 g (0.10 mole) of 3,5-di-tertiary-butyl-p-benzoquinone, 15.1 g (0.11 mole) of m-ethoxyaniline, 125 ml of tetrahydrofuran and 1 ml of boron trifluoride etherate was heated at reflux for about 40 hours. The reaction mixture was evaporated to give an oil which was partitioned between hexane and 10% hydrochloric acid. The hexane phase was dried by filtering through Whatman IPS phase separation filter paper, then evaporated to give a solid. This solid was triturated with hexane, collected, rinsed with hexane, air dried and then recrystallized from ethanol to give a red solid. 1.0 g of this red solid was recrystallized from ethanol to give 0.9 g of red-orange crystalline 2,6-di-tertiary-butyl-4-(3'-ethoxyphenylimino)-2,5-cyclohexadiene-1-one, m.p. 105°-107° C. Calculated for C22H29NO2 : % C, 77.8; % H, 8.6; % N, 4.1; Found: % C, 77.4; % H, 8.5; % H, 3.9.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about 40 hours
  3. customThe reaction mixture was evaporated
  4. customto give an oil which
  5. customwas partitioned between hexane and 10% hydrochloric acid
  6. dry with materialThe hexane phase was dried
  7. filtrationby filtering through Whatman IPS phase separation
  8. filtrationfilter paper
  9. customevaporated
  10. customto give a solid
  11. customThis solid was triturated with hexane
  12. customcollected
  13. washrinsed with hexane, air
  14. customdried
  15. customrecrystallized from ethanol
  16. customto give a red solid
  17. custom1.0 g of this red solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-5ff802efb34a422698f8edd170de17c4
Source dataset
uspto-grants-1987_12
Patent number
US04716178

Reaction notes

Loading…