Hydrochloric Acid → Phenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1,1,3,3-tetramethylbutyl)-

HRID 894272Notes

Reaction equation

HRID 894272 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[N:11][C:12]1[CH:17]=[C:16]([C:18]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:26]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:28])[CH3:27])[C:13]=1[OH:34])([O-])=O.C1(C)C=CC=CC=1.[OH-].[Na+].Cl>[Zn].O.C(O)(C)C>[OH:34][C:13]1[C:14]([C:26]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:28])[CH3:27])=[CH:15][C:16]([C:18]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:19])=[CH:17][C:12]=1[N:11]1[N:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[N:1]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14798Sodium Hydroxide2×HCID 116808Phenol, 2-[(2-nitrophenyl)azo]-4,6-bis(1,1,3,3-tetramethylbutyl)-

Product 1

HCID 116809Phenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1,1,3,3-tetramethylbutyl)-

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst5×HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

To a 5-liter 3-necked flask fitted with a stirrer, thermometer, reflux condenser and nitrogen inlet was charged 400 grams (0.855 mol) of the o-nitroazobenzene intermediate of Example 1 and 1200 ml of toluene. To the resulting solution was added 260 ml of isopropanol and 260 ml of water. A nitrogen atmosphere was imposed and 175 ml of 50.1% aqueous sodium hydroxide was added. A flask containing 170.0 gram (2.6 gram-atoms) of zinc was connected to the reaction flask by Gooch rubber tubing and the zinc dust was added portionwise to the reaction mixture over a 120-minute period. The zinc was added at such a rate to keep the internal temperature at 70° C. After the zinc was all added, an additional 30 ml of 50.1% sodium hydroxide and 20 grams of zinc were added to insure complete reaction. The reaction mixture was heated for 3 hours at 70° C. The mixture was cooled to room temperature by standing overnight and acidified with 500 ml of concentrated hydrochloric acid.

Workup

  1. customTo a 5-liter 3-necked flask fitted with a stirrer
  2. temperaturethermometer, reflux condenser and nitrogen inlet
  3. customat 70° C
  4. customreaction
  5. temperatureThe mixture was cooled to room temperature

Sources & evidence

ORD record
ord-00f51d7b94c14c389b3ccda98599f9ba
Source dataset
uspto-grants-1981_08
Patent number
US04283327

Reaction notes

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