Hydrochloric Acid → HCID 23442887, compound

HRID 2186295Notes

Reaction equation

HRID 2186295 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH:17]([CH3:19])[CH3:18])=[CH:7][C:8]([OH:16])=[C:9]([C:12]=1[CH:13]([CH3:15])[CH3:14])[CH:10]=[O:11])(=[O:3])[CH3:2].[H-].[Na+].[Mg].Br[CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26].Cl>O1CCCC1.O>[C:1]([O:4][C:5]1[C:6]([CH:17]([CH3:19])[CH3:18])=[CH:7][C:8]([OH:16])=[C:9]([CH:10]([OH:11])[CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:12]=1[CH:13]([CH3:15])[CH3:14])(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 157383-BromopentaneHCID 24758Sodium hydrideHCID 5462224MagnesiumHCID 23442868HCID 23442868, compound

Product 1

HCID 23442887HCID 23442887, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Under argon atmosphere, 0.78 g of 5-acetoxy-2-hydroxy-4,6-diisopropylbenzaldehyde was dissolved in 2 ml of anhydrous tetrahydrofuran and a solution of 0.40 g of oily sodium hydride in 1 ml of anhydrous tetrahydrofuran was added. After additional 5 ml of anhydrous tetrahydrofuran was added, the solution was stirred at room temperature for 30 minutes. Then, 5 ml of a Grignard reagent (1.48M in tetrahydrofuran) prepared from magnesium and 3-bromopentane was added dropwise to this reaction solution and the mixture was stirred at room temperature for 2 hours. Then, the mixture was combined with water and 1M hydrochloric acid and extracted with ethyl acetate. The organic layers were washed with saturated brine, then dried over anhydrous magnesium sulfate, and then concentrated. The concentrate as purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate) to give 0.51 g of 4-acetoxy-2-(2-ethyl-1-hydroxybutyl)-3,5-diisopropylphenol as a white amorphous material (yield 51%).

Workup

  1. additionwas added dropwise to this reaction solution
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. concentrationThe concentrate
  8. customas purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate)

Sources & evidence

ORD record
ord-51488c75b4f94585aa1a3321a1fbebc0
Source dataset
uspto-grants-2002_06
Patent number
US06403639B1

Reaction notes

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