Hydrochloric Acid → N,3,5-tritert-butyl-4-hydroxybenzamide

HRID 65723

Reaction equation

HRID 65723 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8](Cl)=[O:9])([CH3:4])([CH3:3])[CH3:2].ClCCl.[C:22]([NH2:26])([CH3:25])([CH3:24])[CH3:23].Cl>C1C=CC=CC=1.CCCCCC>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([NH:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 1203452N,3,5-tritert-butyl-4-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 110624Benzene hexaneSolvent

Procedure

To a stirred solution of 13.43 g. (0.05 mole) of 3,5-di(t-butyl)-4-hydroxybenzoyl chloride in 50 ml. of dichloromethane is added dropwise 8.77 g. (0.12 mole) of t-butylamine. The mixture obtained is neutralized carefully with 10 percent hydrochloric acid and washed thrice with 200 ml. portions of water. The organic layer is dried, then evaporated under vacuum to provide a white residue. The residue is dissolved in hot benzene-hexane mixture and crystallized to provide 3,5-di(t-butyl)-4-hydroxy-N-t-butylbenzamide, m.p. 207°-208° C.

Workup

  1. customThe mixture obtained
  2. washwashed thrice with 200 ml
  3. customThe organic layer is dried
  4. customevaporated under vacuum
  5. customto provide a white residue
  6. customcrystallized

Sources & evidence

ORD record
ord-523687a5a331470bbda2d360c890f3dd
Source dataset
uspto-grants-1978_12
Patent number
US04128664

Linked notes

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