Iodine chloride → 2-Aminomethyl-4-tert-butyl-6-iodophenol hydrochloride

HRID 437205

Reaction equation

HRID 437205 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[OH:14].[I:15]Cl>O.Cl>[ClH:1].[NH2:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:11])([CH3:13])[CH3:12])[CH:7]=[C:6]([I:15])[C:5]=1[OH:14]

Participants

5

Reactant 2

HCID 24640Iodine chlorideHCID 212969502-(Aminomethyl)-4-tert-butylphenol hydrochloride

Product 1

HCID 126342632-Aminomethyl-4-tert-butyl-6-iodophenol hydrochlorideYield 81.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-aminomethyl-4-(1,1-dimethylethyl)phenol hydrochloride (215 g., 1.0 mole) in water (1.6 l.) is added a solution of iodine monochloride (165 g., 1.0 mole) in 3N hydrochloric acid (800 ml.). The resulting reaction mixture is stirred at 20° C. for 3 hours and then cooled to -20° C. whereupon solid is deposited. The deposited solid is collected and crystallized from ethanol 12N-hydrochloric acid (1:1) to give the desired 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol hydrochloride (277 g.), m.p. 200°-201° C. (dec.).

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled to -20° C. whereupon solid
  3. customThe deposited solid is collected
  4. customcrystallized from ethanol 12N-hydrochloric acid (1:1)

Sources & evidence

ORD record
ord-229b6468555249a08a824182d8ff040a
Source dataset
uspto-grants-1977_06
Patent number
US04029816

Linked notes

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