Iodine → 2-Propyl-3-t-butyl-4-hydroxy-5-isopropylphenol

HRID 54625

Reaction equation

HRID 54625 reaction equation
[CH2:1]([C:4]1[C:5](=[O:18])[CH:6]=[C:7]([CH:15]([CH3:17])[CH3:16])[C:8](=[O:14])[C:9]=1[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2][CH3:3].C[SiH](C)O[SiH](C)C.II>C(Cl)Cl>[CH2:1]([C:4]1[C:9]([C:10]([CH3:12])([CH3:11])[CH3:13])=[C:8]([OH:14])[C:7]([CH:15]([CH3:17])[CH3:16])=[CH:6][C:5]=1[OH:18])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 807IodineHCID 186591,1,3,3-Tetramethyl-disiloxaneHCID 570664232-Propyl-3-t-butyl-5-isopropylbenzoquinone

Product 1

HCID 540178862-Propyl-3-t-butyl-4-hydroxy-5-isopropylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 2-propyl-3-t-butyl-5-isopropylbenzoquinone (10 mmol), 1,1,3,3-tetramethyldisiloxane (1.79 mL, 10 mmol) and iodine (0.05 g) in methylene chloride (30 mL). Stir at reflux for 30 minutes and extract with 1N sodium hydroxide (30 mL). Acidify the aqueous phase with concentrated hydrochloric acid and extract into ethyl acetate (4×10 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 2-propyl-3-t-butyl-4-hydroxy-5-isopropylphenol.

Workup

  1. temperatureat reflux for 30 minutes
  2. extractionextract with 1N sodium hydroxide (30 mL)
  3. extractionextract into ethyl acetate (4×10 mL)
  4. dry with materialdry (Na2SO4)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-74f40ec81bdb4a25a8b6d066a07b9c93
Source dataset
uspto-grants-1997_04
Patent number
US05623052

Linked notes

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