Iodine → 4-[(4-Hydroxyphenyl)disulfanyl]phenol

HRID 263301

Reaction equation

HRID 263301 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](=[O:12])(O)[O-].[Na+].II.[I-].[K+]>O.C(O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([S:1][S:1][C:2]2[CH:7]=[CH:6][C:9]([OH:12])=[CH:4][CH:3]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 2401474-MercaptophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 2806654-[(4-Hydroxyphenyl)disulfanyl]phenolYield 97.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-mercaptophenol (200 g., 1.6 m.) in 300 ml. 60% aqueous ethanol was brought to pH 7 by the addition of sodium bicarbonate. A solution of iodine (200 g., 0.8 m.) and potassium iodide (50 g.) in 300 ml. water was added until a yellow end point was reached. The product was filtered off, washed with water and dried. Yield: 97.5%, mp. 144°-6° (lit. 148°-50°). The 1H nmr was consistent with the disulfide structure of the formula: ##STR2##

Workup

  1. filtrationThe product was filtered off
  2. washwashed with water
  3. customdried
  4. customYield: 97.5%, mp. 144°-6° (lit. 148°-50°)

Sources & evidence

ORD record
ord-7a3062d7fc634095b146115138a97834
Source dataset
uspto-grants-1979_05
Patent number
US04156764

Linked notes

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