Hydrochloric Acid → 4-Bromo-2-(3-hydroxy-1,1,3-trimethyl-butyl)-phenol

HRID 395056Notes

Reaction equation

HRID 395056 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8]C(=O)[CH2:6][C:5]2([CH3:14])[CH3:13].[CH2:15]([Mg]Br)C.Cl.C([O:23][CH2:24][CH3:25])(=O)C>O1CCCC1.CCCCCC>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([OH:8])=[C:4]([C:5]([CH3:13])([CH3:14])[CH2:6][C:24]([OH:23])([CH3:25])[CH3:15])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 225689232H-1-Benzopyran-2-one, 6-bromo-3,4-dihydro-4,4-dimethyl-HCID 178418443HCID 178418443, compound

Product 1

HCID 225688104-Bromo-2-(3-hydroxy-1,1,3-trimethyl-butyl)-phenolYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 6-bromo-4,4-dimethyl-chroman-2-one (1 g, 3.92 mmol) in anhydrous tetrahydrofuran (20 mL) was treated with 3M solution of ethyl magnesium bromide (2.6 mL) and stirred at ambient temperature for 2hours. The reaction mixture was poured into cold dilute hydrochloric acid and extracted with ethyl acetate (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a residue which was subjected to flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent to afford the title compound as a pale yellow solid (1.1 g, 100%).

Workup

  1. extractionextracted with ethyl acetate (×2)
  2. extractionThe combined organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a residue which

Sources & evidence

ORD record
ord-5638ca747ccc471cad482618d403e04d
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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