HCID 23442881, compound → HCID 23442862, compound

HRID 2119728Notes

Reaction equation

HRID 2119728 reaction equation
[C:1]([O:4][C:5]1[C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:7][C:8]([OH:14])=[C:9]([C:12]=1[CH3:13])[CH:10]=[O:11])(=[O:3])[CH3:2].[CH:19]([Mg]Br)([CH3:21])[CH3:20]>O1CCCC1>[C:1]([O:4][C:5]1[C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:7][C:8]([OH:14])=[C:9]([CH:10]([OH:11])[CH:19]([CH3:21])[CH3:20])[C:12]=1[CH3:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 23442881HCID 23442881, compoundHCID 178418365HCID 178418365, compound

Product 1

HCID 23442862HCID 23442862, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon atmosphere, 5-acetoxy-4-t-butyl-2-hydroxy-6-methylbenzaldehyde was dissolved in 10 ml of anhydrous tetrahydrofuran, 10 ml of isopropylmagnesium bromide (0.76M in tetrahydrofuran) was added dropwise and the mixture was stirred at room temperature for 30 minutes. After the reaction was quenched with distilled water, the reaction mixture was combined with IN hydrochloric acid and extracted with ethyl acetate. The organic layers were washed with saturated brine, then dried over anhydrous magnesium sulfate, and then concentrated to give 0.44 g of 4-acetoxy-5-t-butyl-2-(1-hydroxy-2-methylpropyl)-3-methylphenol as a yellow amorphous material (yield 100%).

Workup

  1. customAfter the reaction was quenched with distilled water
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-97bd7aca0ec644e0a1f9ec972b0e360b
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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