Hydrochloric Acid → HCID 19775705, compound

HRID 1032827Notes

Reaction equation

HRID 1032827 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.Cl>O1CCCC1>[C:1]([C:5]1[CH:6]=[C:7]([N:8]2[C:20](=[O:21])[C:19]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]3[C:17]2=[O:22])[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6811Phthalic AnhydrideHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 19775705HCID 19775705, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8.8 g (40 mmol) of 3,5-di-tert-butyl-4-hydroxyaniline and 5.9 g (40 mmol) of phthalic anhydride in 100 ml of tetrahydrofuran was refluxed for 24 hours. Concentrated hydrochloric acid (0.5 ml) was added and the mixture was refluxed for an additional seventeen hours and concentrated in vacuo. The resulting solid (13.2 g) was washed successively with water and hexane and then recrystallized from acetone-hexane to yield 10.9 g (31 mmol, 77%) of N-(3,5-di-tert-butyl-4-hydroxyphenyl)phthalimide, mp 196°-201° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturethe mixture was refluxed for an additional seventeen hours
  3. concentrationconcentrated in vacuo
  4. washThe resulting solid (13.2 g) was washed successively with water and hexane
  5. customrecrystallized from acetone-hexane

Sources & evidence

ORD record
ord-b984a580510340f9abd09018a0b64d97
Source dataset
uspto-grants-1990_09
Patent number
US04959482

Reaction notes

Loading…