Hydrochloric Acid → HCID 20395011, compound

HRID 261407Notes

Reaction equation

HRID 261407 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)([O-:23])=[O:22].Cl>CCCCCC.ClCCl.C(COC)OC>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([C:28]([C:9]2[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:15])=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=2)=[O:29])=[CH:31][CH:32]=1)([O-:23])=[O:22]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 314052,6-Di-tert-butylphenolHCID 178418339Butyllithium

Product 1

HCID 20395011HCID 20395011, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2,6-di(t-butyl)phenol in 150 ml. of glyme under nitrogen is added 52 ml. of 2.04 M n-butyl lithium in hexane. The reaction causes an exotherm and the product is heated to 60° C. About 20 g. of 4-nitrobenzoyl chloride is added, and the resulting solution is stirred without heating for about 16 hours. The mixture is then acidified with 10 percent hydrochloric acid and washed with dichloromethane, then with 10 percent sodium hydroxide solution and finally with water. The solution is then reacted in ethanol with 50 percent sodium hydroxide solution by heating at reflux for about two hours, mixed with dichloromethane, then washed several times with water. The organic layer is separated, dried and evaporated to provide an orange oil which solidifies in cold hexane. This solid is recrystallized from a benzene-hexane mixture to provide 4-(4-nitrobenzoyl)-2,6-di(t-butyl)phenol, m.p. 178°-179.5° C.

Workup

  1. temperaturewithout heating for about 16 hours
  2. washwashed with dichloromethane
  3. customThe solution is then reacted in ethanol with 50 percent sodium hydroxide solution
  4. temperatureby heating
  5. temperatureat reflux for about two hours
  6. washwashed several times with water
  7. customThe organic layer is separated
  8. customdried
  9. customevaporated
  10. customto provide an orange oil which
  11. customThis solid is recrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-2c8fe0128eb24ffa89dd61ff2e19cff8
Source dataset
uspto-grants-1979_08
Patent number
US04165383

Reaction notes

Loading…