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

HRID 24094Notes

Reaction equation

HRID 24094 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 2 hours. 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-4ba4a100b0a84178b00d79f0a4b0d85d
Source dataset
uspto-grants-2005_02
Patent number
US06855512B2

Reaction notes

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